JP5915383B2 - Cyclohexanone compound and herbicide containing the same - Google Patents

Description

  The present invention relates to a cyclohexanone compound and a herbicide containing the same.

Until now, the development of compounds as active ingredients of herbicides for controlling weeds has been widely promoted, and compounds having the effect of controlling weeds have been found.
Cyclohexanone compounds (Patent Documents 1 to 8) having herbicidal activity are known.

USP 4,209,532 USP 4,303,669 USP 4,351,666 USP 4,409,513 USP 4,659,372 WO 2001/017972 WO 2003/059065 WO 2008/110308 WO 2010/046194

  An object of the present invention is to provide a compound having an excellent weed control effect.

［式中、
ｍは１、２又は３の整数を表し、
ｎは１〜５いずれかの整数を表し、
ＸはＣＨ_2、Ｏ、ＮＲ⁹、Ｓ、Ｓ（Ｏ）又はＳ（Ｏ）₂を表し、
Ｒ¹は水素またはメチル基を表し、
Ｒ²及びＲ³は、互いに独立に、水素、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_3-8ハロシクロアルキル基、（Ｃ_1-6アルキル）Ｃ_3-8シクロアルキル基、（Ｃ_3-8シクロアルキル）Ｃ_1-6アルキル基、（Ｃ_3-8シクロアルキル）Ｃ_3-8シクロアルキル基、（Ｃ_3-8ハロシクロアルキル）Ｃ_1-6アルキル基、｛（Ｃ_1-6アルキル）Ｃ_3-8シクロアルキル｝Ｃ_1-6アルキル基を表すか、Ｒ²とＲ³とが結合してＣ_2-5アルキレン鎖を表すか、又はＲ²とＲ³とが一緒になってハロゲンを有していてもよいＣ_1-3アルキリデン基を表し（但し、ｍが２又は３である場合、２又は３個のＲ²は同一であっても異なっていてもよく、２又は３個のＲ³は同一であっても異なっていてもよい。）、
Ｒ⁴はＣ_6-10アリール基又は５〜６員のヘテロアリール基を表し（但し、該Ｃ_6-10アリール基及び５〜６員のヘテロアリール基はハロゲン、シアノ基、ニトロ基、アミノ基、（Ｃ_1-6アルキル）アミノ基、（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノ基、ベンゾイルアミノ基、アミノカルボニル基、（Ｃ_1-6アルキル）アミノカルボニル基、（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノカルボニル基、ペンタフルオロチオ基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_3―6アルケニルオキシ基、Ｃ_3―6アルキニルオキシ基、Ｃ_6-10アリール基、Ｃ_6-10アリールオキシ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基、ヒドロキシル基、（Ｃ_1-6アルキル）カルボニル基、ヒドロキシカルボニル基、（Ｃ_1-6アルコキシ）カルボニル基及び（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基からなる群から選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。また、該（Ｃ_1-6アルキル）アミノ基、（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノ基、ベンゾイルアミノ基、（Ｃ_1-6アルキル）アミノカルボニル基、（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノカルボニル基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_3―6アルケニルオキシ基、Ｃ_3―6アルキニルオキシ基、Ｃ_6-10アリール基、Ｃ_6-10アリールオキシ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基、（Ｃ_1-6アルコキシ）カルボニル基及び（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基は１以上のハロゲンまたはＣ_1-3ハロアルキル基を有していてもよく、２以上のハロゲンまたはＣ_1-3ハロアルキル基を有している場合、該ハロゲンまたはＣ_1-3ハロアルキル基は同一であっても異なっていてもよい。）、
Ｇは水素又は下記式

｛式中、Ｌは酸素またはイオウを表し、
Ｒ⁵はＣ_1-6アルキル基、Ｃ_3-8シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_6-10アリール基、（Ｃ_6-10アリール）Ｃ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_3-8シクロアルコキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基、（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノ基、（Ｃ_3-6アルケニル）（Ｃ_3-6アルケニル）アミノ基、（Ｃ_1-6アルキル）（Ｃ_6-10アリール）アミノ基又は５〜６員のヘテロアリール基を表し（但し、これらはいずれも１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。また、該Ｃ_3-8シクロアルキル基、Ｃ_6-10アリール基、（Ｃ_6-10アリール）Ｃ_1-6アルキル基のアリール部分、Ｃ_3-8シクロアルコキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基のアリール部分、（Ｃ_1-6アルキル）（Ｃ_6-10アリール）アミノ基のアリール部分及び５〜６員のヘテロアリール基はいずれも１以上のＣ_1-6アルキル基を有していてもよく、２以上のＣ_1-6アルキル基を有している場合、該アルキル基は同一であっても異なっていてもよい。）、
Ｒ⁶はＣ_1-6アルキル基、Ｃ_6-10アリール基又は（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノ基を表し(但し、これらはいずれも１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。また、該Ｃ_6-10アリール基は１以上のＣ_1-6アルキル基を有していてもよく、２以上のＣ_1-6アルキル基を有している場合、該アルキル基は同一であっても異なっていてもよい。)、
Ｒ⁷は水素又はＣ_1-6アルキル基を表し、
ＷはＣ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基を表す（但し、これらはいずれも１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。）。｝
で表されるいずれかの基を表し、
Ｒ⁹は、水素、Ｃ_1-6アルキル基、Ｃ_6-10アリール基、Ｃ_6-10アリールチオ基、Ｃ_6-10アリールスルフィニル基、又はＣ_6-10アリールスルホニル基を表し（但し、該Ｃ_1-6アルキル基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。該Ｃ_6-10アリール基、Ｃ_6-10アリールチオ基、Ｃ_6-10アリールスルフィニル基、Ｃ_6-10アリールスルホニル基はハロゲン、シアノ基、ニトロ基、アミノ基からなる群から選ばれる１以上の置換基を有していてもよい。）
Ｚはハロゲン、シアノ基、ニトロ基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、（Ｃ_1-6アルキル）カルボニル基、Ｃ_1-6アルキルチオ基、Ｃ_6-10アリールオキシ基、５〜６員のヘテロアリールオキシ基、Ｃ_3-8シクロアルキル基、Ｃ_6-10アリール基又は５〜６員のヘテロアリール基を表し、（但し、該Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、（Ｃ_1-6アルキル）カルボニル基、及びＣ_1-6アルキルチオ基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。該Ｃ_6-10アリール基、５〜６員のヘテロアリール基、Ｃ_6-10アリールオキシ基、及び５〜６員のヘテロアリールオキシ基はハロゲン、Ｃ_1-6アルキル基及びＣ_1-6ハロアルキル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。該Ｃ_3-8シクロアルキル基はハロゲン及びＣ_1-6アルキル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。さらに、ｎが２以上の整数を表わす場合、Ｚは同一であっても異なっていてもよい。）。〕
で示されるシクロヘキサノン化合物。
［項２］ ｎが１〜３いずれかの整数であり、
Ｒ¹が水素であり、
Ｒ²及びＲ³は、互いに独立に、水素、Ｃ_1-3アルキル基又はＲ²とＲ³とが結合してＣ_2-5アルキレン鎖であり（但し、ｍが２又は３である場合、２又は３個のＲ²は同一であっても異なっていてもよく、２又は３個のＲ³は同一であっても異なっていてもよい。）、
Ｒ⁴がフェニル基、２−ピリジル基、３−ピリジル基、４−ピリジル基、２−ピリミジニル基、２−ピラジニル基、３−ピリダジニル基、３−フリル基、２−チエニル基、２−チアゾリル基、１，２，３−トリアゾリル基又は１−ピラゾリル基であり（但し、該フェニル基、２−ピリジル基、３−ピリジル基、４−ピリジル基、２−ピリミジニル基、２−ピラジニル基、３−ピリダジニル基、３−フリル基、２−チエニル基及び２−チアゾリル基は、ハロゲン、Ｃ_1-3アルキル基、ヒドロキシル基、（Ｃ_1-3アルキル）カルボニル基、（Ｃ_1-3アルコキシ）カルボニル基、Ｃ_1-3アルコキシ基、Ｃ_1-3ハロアルキル基、Ｃ_1-3アルキルチオ基、Ｃ_1-3ハロアルキルチオ基、シアノ基、ニトロ基、アミノ基、ペンタフルオロチオ基、ベンゾイルアミノ基及びＣ_1-3ハロアルコキシ基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。また該１，２，３−トリアゾリル基及び１−ピラゾリル基は、Ｃ_1-3アルキル基及びＣ_6-10アリール基からなる群より選ばれる１以上の置換基を有していてもよく、該Ｃ_1-3アルキル基及びＣ_6-10アリール基は、１以上のハロゲンまたは１以上のＣ_1-3ハロアルキル基を有していてもよく、２以上のハロゲンまたは２以上のＣ_1-3ハロアルキル基を有している場合、該ハロゲンまたはＣ_1-3ハロアルキル基は同一であっても異なっていてもよい。）、
Ｇが水素又は下記式

｛式中、Ｒ^5aはＣ_1-6アルキル基、Ｃ_6-10アリール基、Ｃ_1-6アルコキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基又はＣ_6-10アリールオキシ基を表し、
Ｒ^6aはＣ_1-6アルキル基を表し、
Ｗ^aはＣ_1-3アルコキシ基を表す。｝
で表されるいずれかの基であり、
Ｒ⁹が、水素、Ｃ_1-6アルキル基又はＣ_6-10アリールスルホニル基であり（但し、該Ｃ_1-6アルキル基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。該Ｃ_6-10アリールスルホニル基は、ハロゲン及びニトロ基からなる群から選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。）、
Ｚがハロゲン、Ｃ_1-3アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-3アルコキシ基、Ｃ_3-8シクロアルキル基、ニトロ基、フェニル基又は５〜６員のヘテロアリールオキシ基（但し、該Ｃ_1-3アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-3アルコキシ基、フェニル基及び５〜６員のヘテロアリールオキシ基は、１以上のハロゲンを有していてもよく。２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。）である、［項１］記載のシクロヘキサノン化合物。
［項３］ ｍが２であり、
Ｒ²及びＲ³は、互いに独立に、水素、メチル基、エチル基又はＲ²とＲ³とが結合してエチレン鎖であり（但し、２個のＲ²は同一であっても異なっていてもよく、また、２個のＲ³は同一であっても異なっていてもよい。）、
Ｒ⁴がフェニル基、２−ピリジル基、３−ピリジル基、４−ピリジル基、２−ピリミジニル基、２−ピラジニル基、３−ピリダジニル基、３−フリル基、２−チエニル基、２−チアゾリル基、１，２，３−トリアゾリル基又は１−ピラゾリル基であり（但し、該フェニル基、２−ピリジル基、３−ピリジル基、４−ピリジル基、２−ピリミジニル基、２−ピラジニル基、３−ピリダジニル基、３−フリル基、２−チエニル基及び２−チアゾリル基は、塩素、臭素、ヨウ素、フッ素、メチル基、エチル基、イソプロピル基、ｔ−ブチル基、メトキシ基、ニトロ基、アミノ基、シアノ基、ヒドロキシル基、アセチル基、メトキシカルボニル基、ペンタフルオロチオ基、ペンタフルオロエチル基、ジフルオロエチル基、ヘプタフルオロイソプロピル基、トリフルオロメチルチオ基、ベンゾイルアミノ基、トリフルオロメトキシ基及びトリフルオロメチル基からなる群より選ばれる１以上の置換基を有している。また該１，２，３−トリアゾリル基及び１−ピラゾリル基は、メチル基及びフェニル基からなる群より選ばれる１以上の置換基を有していてもよく、該フェニル基は、塩素、臭素、ヨウ素、フッ素及びトリフルオロメチル基からなる群より選ばれる１以上の置換基を有していてもよい。）、
Ｇが水素、アセチル基、プロピオニル基、ブチルカルボニル基、ベンゾイル基、メチルスルホニル基、メトキシカルボニル基、エトキシカルボニル基、アリルオキシカルボニル基、フェノキシカルボニル基、メトキシメチル基又はエトキシメチル基であり、
Ｒ⁹が水素、２−ニトロフェニルスルホニル基又はメチル基であり、
Ｚがメチル基、エチル基、フェニル基、ビニル基、シクロプロピル基、ニトロ基、フッ素、塩素、臭素、メトキシ基、トリフルオロメチル基、５−トリフルオロメチル−２−クロロピリジルオキシ基又はエチニル基である、［項２］記載のシクロヘキサノン化合物。
［項４］ 式（ＩＩ）

［式中、
ｐは１、２又は３の整数を表し、
ｑは１〜５いずれかの整数を表し、
Ｘ^bはＣＨ₂、Ｏ、Ｓ、Ｓ（Ｏ）又はＳ（Ｏ）₂を表し、
Ｒ^1bは水素またはメチル基を表し、
Ｒ^2b及びＲ^3bは、互いに独立に、水素、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_3-8ハロシクロアルキル基、（Ｃ_1-6アルキル）Ｃ_3-8シクロアルキル基、（Ｃ_3-8シクロアルキル）Ｃ_1-6アルキル基、（Ｃ_3-8シクロアルキル）Ｃ_3-8シクロアルキル基、（Ｃ_3-8ハロシクロアルキル）Ｃ_1-6アルキル基、｛（Ｃ_1-6アルキル）Ｃ_3-8シクロアルキル｝Ｃ_1-6アルキル基を表すか、Ｒ^2bとＲ^3bとが結合してＣ_2-5アルキレン鎖を表すか、又はＲ^2bとＲ^3bとが一緒になってハロゲンを有していてもよいＣ_1-3アルキリデン基を表し（但し、ｐが２又は３である場合、２又は３個のＲ^2bは同一であっても異なっていてもよく、２又は３個のＲ^3bは同一であっても異なっていてもよい。）、
Ｒ^4bはＣ_6-10アリール基又は５〜６員のヘテロアリール基を表わし（但し、該Ｃ_6-10アリール基および５〜６員のヘテロアリール基はハロゲン、シアノ基、ニトロ基、ペンタフルオロチオ基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_3―6アルケニルオキシ基、Ｃ_3―6アルキニルオキシ基及び（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基からなる群から選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。また、該Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_3―6アルケニルオキシ基、Ｃ_3―6アルキニルオキシ基及び（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。）、
Ｇ^bは水素又は下記式

｛式中、Ｌ^bは酸素またはイオウを表し、
Ｒ^5bはＣ_1-6アルキル基、Ｃ_3-8シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_6-10アリール基、（Ｃ_6-10アリール）Ｃ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_3-8シクロアルコキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基、（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノ基、（Ｃ_3-6アルケニル）（Ｃ_3-6アルケニル）アミノ基、（Ｃ_1-6アルキル）（Ｃ_6-10アリール）アミノ基又は５〜６員のヘテロアリール基を表し（但し、これらはいずれも１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。また、該Ｃ_3-8シクロアルキル基、Ｃ_6-10アリール基、（Ｃ_6-10アリール）Ｃ_1-6アルキル基のアリール部分、Ｃ_3-8シクロアルコキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基のアリール部分、（Ｃ_1-6アルキル）（Ｃ_6-10アリール）アミノ基のアリール部分及び５〜６員のヘテロアリール基はいずれも１以上のＣ_1-6アルキル基を有していてもよく、２以上のＣ_1-6アルキル基を有している場合、該アルキル基は同一であっても異なっていてもよい。）、
Ｒ^6bはＣ_1-6アルキル基、Ｃ_6-10アリール基又は（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノ基を表し(但し、これらはいずれも１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。また、該Ｃ_6-10アリール基は１以上のＣ_1-6アルキル基を有していてもよく、２以上のＣ_1-6アルキル基を有している場合、該アルキル基は同一であっても異なっていてもよい。)、
Ｒ^7bは水素又はＣ_1-6アルキル基を表し、
Ｗ^bはＣ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基を表す（但し、これらはいずれも１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。）。｝
で表されるいずれかの基を表し、
Ｚ^bはハロゲン、シアノ基、ニトロ基、フェニル基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_6-10アリールオキシ基、５〜６員のヘテロアリールオキシ基又はＣ_3-8シクロアルキル基を表す（但し、該Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、及びＣ_1-6アルキルチオ基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。該フェニル基、Ｃ_6-10アリールオキシ基、及び５〜６員のヘテロアリールオキシ基はハロゲン、Ｃ_1-6アルキル基及びＣ_1-6ハロアルキル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。該Ｃ_3-8シクロアルキル基はハロゲン及びＣ_1-6アルキル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。さらに、ｑが２以上の整数を表わす場合、Ｚ^bは同一であっても異なっていてもよい。）。〕
で示されるシクロヘキサノン化合物。
［項５］ ｎが１〜３いずれかの整数であり、
Ｒ^1bが水素であり、
Ｒ^2b及びＲ^3bが、互いに独立に、水素又はＣ_1-3アルキル基であり（但し、ｐが２又は３である場合、２又は３個のＲ^2bは同一であっても異なっていてもよく、２又は３個のＲ^3bは同一であっても異なっていてもよい。）、
Ｒ^4bがフェニル基又は２−ピリジル基であり（但し、該フェニル基及び２−ピリジル基はハロゲン、Ｃ_1-3アルキル基、Ｃ_1-3アルコキシ基、Ｃ_1-3ハロアルキル基、ニトロ基、ペンタフルオロチオ基、Ｃ_1-3ハロアルコキシ基からなる群から選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。）、
Ｇ^bが水素又は下記式

｛式中、Ｒ^5aはＣ_1-6アルキル基、Ｃ_6-10アリール基、Ｃ_1-6アルコキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基又はＣ_6-10アリールオキシ基を表し、
Ｗ^aはＣ_1-3アルコキシ基を表す。｝
で表されるいずれかの基であり、
Ｚ^bがＣ_1-3アルキル基である、［項４］記載のシクロヘキサノン化合物。
［項６］ ｐが２であり、
Ｒ^2b及びＲ^3bは、互いに独立に、水素又はメチル基であり（但し、２個のＲ^2bは同一であっても異なっていてもよく、また、２個のＲ^3bは同一であっても異なっていてもよい。）、
Ｒ^4bがフェニル基または２−ピリジル基であり（ただし、該フェニル基及び２−ピリジル基は塩素、フッ素、メチル基、メトキシ基及びトリフルオロメチル基からなる群から選ばれる１以上の置換基を有している。）、
Ｇ^bが水素、アセチル基、プロピオニル基、ベンゾイル基、メトキシカルボニル基、エトキシカルボニル基、アリルオキシカルボニル基、フェノキシカルボニル基、メトキシメチル基又はエトキシメチル基であり、
Ｚ^bがメチル基又はエチル基である、［項５］記載のシクロヘキサノン化合物。
［項７］ Ｇが水素である［項１］〜［項６］のいずれか１つに記載のシクロヘキサノン化合物。
［項８］ ［項１］〜［項７］のいずれか１つに記載のシクロヘキサノン化合物を有効成分として含有する除草剤。
［項９］ ［項１］〜［項７］のいずれか１つに記載のシクロヘキサノン化合物の有効量を、雑草または雑草の生育する土壌に施用する雑草の防除方法。
［項１０］ 雑草を防除するための［項１］〜［項７］のいずれか１つに記載のシクロヘキサノン化合物の使用。 As a result of intensive studies, the present inventors have found that a cyclohexanone compound represented by the following formula (I) has an excellent weed control effect, and have reached the present invention.
[Term 1] Formula (I)

[Where:
m represents an integer of 1, 2 or 3,
n represents an integer of 1 to 5,
X represents CH _2, O, NR ⁹ , S, S (O) or S (O) ₂ ;
R ¹ represents hydrogen or a methyl group;
R ² and R ³ are independently of each other hydrogen, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, (C _1-6 alkyl) ) C _3-8 cycloalkyl group, (C _3-8 cycloalkyl) C _1-6 alkyl group, (C _3-8 cycloalkyl) C _3-8 cycloalkyl group, (C _3-8 halocycloalkyl) C _1-6 alkyl group, {(C _1-6 alkyl) C _3-8 cycloalkyl} represents a C _1-6 alkyl group, or R ² and R ³ combine to represent a C _2-5 alkylene chain Or R ² and R ³ together represent a C _1-3 alkylidene group which may have a halogen (provided that when m is 2 or 3, two or three R ² are the same) Or two or three R ^{3 s} may be the same or different).
R ⁴ represents a C _6-10 aryl group or a 5-6 membered heteroaryl group (provided that the C _6-10 aryl group and the 5-6 membered heteroaryl group are halogen, cyano group, nitro group, amino group) , (C _1-6 alkyl) amino group, (C _1-6 alkyl) (C _1-6 alkyl) amino group, benzoylamino group, aminocarbonyl group, (C _1-6 alkyl) aminocarbonyl group, (C _{1 -6} alkyl) (C _1-6 alkyl) aminocarbonyl group, pentafluorothio group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, C _{1 -6} alkylthio group, C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, C _6-10 aryl group, C _6-10 aryloxy group, C _1-6 alkylsulfinyl group, C _1-6 alkylsulfonyl group, a hydroxyl group, (C _1-6 alkyl) carbonyl group, human Butyloxycarbonyl group, may have one or more substituents selected from the group consisting of (C _1-6 alkoxy) carbonyl group, and (C _6-10 aryl) C _1-6 alkoxy group, two or more substituents In the case of having a group, the substituents may be the same or different, and the (C _1-6 alkyl) amino group, (C _1-6 alkyl) (C _1-6 alkyl) Amino group, benzoylamino group, (C _1-6 alkyl) aminocarbonyl group, (C _1-6 alkyl) (C _1-6 alkyl) aminocarbonyl group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, C _1-6 alkylthio group, C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, C _6-10 aryl group, C _6-10 aryloxy group, C _1-6 alkylsulfinyl group, C _1-6 alkylsulfonyl group, (C _1-6 alkoxy ) Carbonyl group, and (C _6-10 aryl) C _1-6 alkoxy group may have one or more halogen or C _1-3 haloalkyl group, have a 2 or more halogen or C _1-3 haloalkyl group The halogen or C _1-3 haloalkyl groups may be the same or different).
G is hydrogen or the following formula

{Wherein L represents oxygen or sulfur,
R ⁵ is C _1-6 alkyl group, C _3-8 cycloalkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _6-10 aryl group, (C _6-10 aryl) C _1-6 Alkyl group, C _1-6 alkoxy group, C _3-8 cycloalkoxy group, C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 alkoxy group, (C _1-6 alkyl) (C _1-6 alkyl) amino group, (C _3-6 alkenyl) (C _3-6 alkenyl) amino group, (C _1-6 alkyl) (C _{6 -10} aryl) represents an amino group or a 5- to 6-membered heteroaryl group (provided that each of these may have one or more halogens, and when having two or more halogens, the halogen is it may be the same or different. Furthermore, the C _3-8 cycloalkyl group, C _6-10 aryl group, (C _6-10 aryl) C _1-6 a Aryl moiety of the kill group, C _3-8 cycloalkoxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 aryl moiety of alkoxy groups, (C _1-6 alkyl) (C _{6- 10} aryl) The aryl part of the amino group and the 5-6 membered heteroaryl group may each have one or more C _1-6 alkyl groups, and have two or more C _1-6 alkyl groups. The alkyl groups may be the same or different).
R ⁶ represents a C _1-6 alkyl group, a C _6-10 aryl group or a (C _1-6 alkyl) (C _1-6 alkyl) amino group (provided that each of these has one or more halogens) In the case of having two or more halogens, the halogens may be the same or different, and the C _6-10 aryl group has one or more C _1-6 alkyl groups. And when having two or more C _1-6 alkyl groups, the alkyl groups may be the same or different).
R ⁷ represents hydrogen or a C _1-6 alkyl group,
W represents a C _1-6 alkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, or a C _1-6 alkylsulfonyl group (provided that any of these may have one or more halogens) In the case of having two or more halogens, the halogens may be the same or different.) }
Any one of the groups represented by
R ⁹ represents hydrogen, a C _1-6 alkyl group, a C _6-10 aryl group, a C _6-10 arylthio group, a C _6-10 arylsulfinyl group, or a C _6-10 arylsulfonyl group (provided that the C _1-6 alkyl group may have one or more halogen atoms, and when two or more halogens, the halogens may be the same or different. the C _6-10 aryl group , C _6-10 arylthio group, C _6-10 arylsulfinyl group, C _6-10 arylsulfonyl group have one or more substituents selected from the group consisting of halogen, cyano group, nitro group and amino group. May be good.)
Z is halogen, cyano group, nitro group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, (C _1-6 alkyl) carbonyl group, C _{1 -6} alkylthio group, C _6-10 aryloxy group, 5-6 membered heteroaryloxy group, C _3-8 cycloalkyl group, C _6-10 aryl group or 5-6 membered heteroaryl group; However, the C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, (C _1-6 alkyl) carbonyl group, and C _1-6 alkylthio group are 1 The halogen atom may be the same or different when it has two or more halogen atoms, the C _6-10 aryl group, a 5- to 6-membered hetero group. Aryl, C _6-10 aryloxy, and 5-6 membered heteroaryloxy groups are halogen, C _It may have one or more substituents selected from the group consisting of a _1-6 alkyl group and a C _1-6 haloalkyl group, and when it has two or more substituents, the substituents are the same. The C _3-8 cycloalkyl group may have one or more substituents selected from the group consisting of halogen and C _1-6 alkyl groups, and may have two or more substituents. And the substituents may be the same or different, and when n represents an integer of 2 or more, Z may be the same or different.) ]
A cyclohexanone compound represented by:
[Claim 2] n is an integer of 1 to 3,
R ¹ is hydrogen;
R ² and R ³ are independently of each other hydrogen, a C _1-3 alkyl group, or R ² and R ³ are combined to form a C _2-5 alkylene chain (provided that when m is 2 or 3, 2 or 3 R ² may be the same or different, and 2 or 3 R ³ may be the same or different.)
R ⁴ is phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3-pyridazinyl group, 3-furyl group, 2-thienyl group, 2-thiazolyl group. 1,2,3-triazolyl group or 1-pyrazolyl group (provided that the phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3- The pyridazinyl group, 3-furyl group, 2-thienyl group and 2-thiazolyl group are halogen, C _1-3 alkyl group, hydroxyl group, (C _1-3 alkyl) carbonyl group, (C _1-3 alkoxy) carbonyl group. , C _1-3 alkoxy, C _1-3 haloalkyl group, C _1-3 alkylthio group, C _1-3 haloalkylthio group, a cyano group, a nitro group, an amino group, pentafluoro thio group, benzoylamino Moto及May optionally have one or more substituents selected from the group consisting of C _1-3 haloalkoxy groups, and when two or more substituents, the substituents optionally substituted by one or more identical The 1,2,3-triazolyl group and 1-pyrazolyl group may have one or more substituents selected from the group consisting of a C _1-3 alkyl group and a C _6-10 aryl group. The C _1-3 alkyl group and the C _6-10 aryl group may have one or more halogens or one or more C _1-3 haloalkyl groups, and may have two or more halogens or two or more C _{1. -3} haloalkyl group, the halogen or C _1-3 haloalkyl group may be the same or different).
G is hydrogen or the following formula

{Wherein R ^5a represents a C _1-6 alkyl group, a C _6-10 aryl group, a C _1-6 alkoxy group, a C _3-6 alkenyloxy group, a C _3-6 alkynyloxy group or a C _6-10 aryloxy group. Represents a group,
R ^6a represents a C _1-6 alkyl group,
W ^a represents ^a C _1-3 alkoxy group. }
Any of the groups represented by
R ⁹ is hydrogen, a C _1-6 alkyl group or a C _6-10 arylsulfonyl group (provided that the C _1-6 alkyl group may have one or more halogen atoms, and And the halogen may be the same or different, and the C _6-10 arylsulfonyl group has one or more substituents selected from the group consisting of halogen and nitro group. And when it has two or more substituents, the substituents may be the same or different).
Z is halogen, C _1-3 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-3 alkoxy group, C _3-8 cycloalkyl group, nitro group, phenyl group or 5-6 membered A heteroaryloxy group (provided that the C _1-3 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-3 alkoxy group, phenyl group and 5- to 6-membered heteroaryloxy group are The cyclohexanone compound according to [1], which may have one or more halogens, and when two or more halogens are present, the halogens may be the same or different. .
[Section 3] m is 2,
R ² and R ³ are independently of each other hydrogen, methyl group, ethyl group, or R ² and R ³ are combined to form an ethylene chain (provided that two R ² are the same or different. And the two R ³ groups may be the same or different.)
R ⁴ is phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3-pyridazinyl group, 3-furyl group, 2-thienyl group, 2-thiazolyl group. 1,2,3-triazolyl group or 1-pyrazolyl group (provided that the phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3- Pyridazinyl group, 3-furyl group, 2-thienyl group and 2-thiazolyl group are chlorine, bromine, iodine, fluorine, methyl group, ethyl group, isopropyl group, t-butyl group, methoxy group, nitro group, amino group, Cyano group, hydroxyl group, acetyl group, methoxycarbonyl group, pentafluorothio group, pentafluoroethyl group, difluoroethyl group, heptafluoroisopropyl And having one or more substituents selected from the group consisting of trifluoromethylthio group, benzoylamino group, trifluoromethoxy group, and trifluoromethyl group, and 1,2,3-triazolyl group and 1-pyrazolyl group The group may have one or more substituents selected from the group consisting of a methyl group and a phenyl group, and the phenyl group is selected from the group consisting of chlorine, bromine, iodine, fluorine and trifluoromethyl groups. One or more substituents may be present).
G is hydrogen, acetyl group, propionyl group, butylcarbonyl group, benzoyl group, methylsulfonyl group, methoxycarbonyl group, ethoxycarbonyl group, allyloxycarbonyl group, phenoxycarbonyl group, methoxymethyl group or ethoxymethyl group,
R ⁹ is hydrogen, 2-nitrophenylsulfonyl group or methyl group,
Z is methyl, ethyl, phenyl, vinyl, cyclopropyl, nitro, fluorine, chlorine, bromine, methoxy, trifluoromethyl, 5-trifluoromethyl-2-chloropyridyloxy or ethynyl The cyclohexanone compound according to [Item 2], wherein
[Item 4] Formula (II)

[Where:
p represents an integer of 1, 2 or 3,
q represents an integer of 1 to 5,
X ^b represents CH ₂ , O, S, S (O) or S (O) ₂ ;
R ^1b represents hydrogen or a methyl group,
R ^2b and R ^3b are independently of each other hydrogen, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, (C _1-6 alkyl) ) C _3-8 cycloalkyl group, (C _3-8 cycloalkyl) C _1-6 alkyl group, (C _3-8 cycloalkyl) C _3-8 cycloalkyl group, (C _3-8 halocycloalkyl) C _1-6 alkyl group, {(C _1-6 alkyl) C _3-8 cycloalkyl} represents a C _1-6 alkyl group, or R ^2b and R ^3b are combined to represent a C _2-5 alkylene chain Or R ^2b and R ^3b together represent a C _1-3 alkylidene group which may have a halogen (provided that when p is 2 or 3, 2 or 3 R ^2b are the same) Or two or three R ^3b may be the same or different.),
R ^4b represents a C _6-10 aryl group or a 5-6 membered heteroaryl group (provided that the C _6-10 aryl group and the 5-6 membered heteroaryl group are halogen, cyano group, nitro group, pentafluoro Thio group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, C _1-6 alkylthio group, C _3-6 alkenyloxy group, C _3-6 It may have one or more substituents selected from the group consisting of an alkynyloxy group and a (C _6-10 aryl) C _1-6 alkoxy group, and when it has two or more substituents, The groups may be the same or different, and the C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, C _1-6 alkylthio group , C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, and (C _6-10 aryl) C _1-6 Al Alkoxy group may have one or more halogen atoms, and when two or more halogens, the halogens may be the same or different.),
G ^b is hydrogen or the following formula

{Wherein L ^b represents oxygen or sulfur;
R ^5b is a C _1-6 alkyl group, C _3-8 cycloalkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _6-10 aryl group, (C _6-10 aryl) C _1-6 Alkyl group, C _1-6 alkoxy group, C _3-8 cycloalkoxy group, C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 alkoxy group, (C _1-6 alkyl) (C _1-6 alkyl) amino group, (C _3-6 alkenyl) (C _3-6 alkenyl) amino group, (C _1-6 alkyl) (C _{6 -10} aryl) represents an amino group or a 5- to 6-membered heteroaryl group (provided that each of these may have one or more halogens, and when having two or more halogens, the halogen is The C _3-8 cycloalkyl group, C _6-10 aryl group, (C _6-10 aryl) C _1-6 a may be the same or different. Aryl moiety of alkyl group, C _3-8 cycloalkoxy group, C _6-10 aryloxy group, aryl part of (C _6-10 aryl) C _1-6 alkoxy group, (C _1-6 alkyl) (C _{6- 10} aryl) The aryl part of the amino group and the 5-6 membered heteroaryl group may each have one or more C _1-6 alkyl groups, and have two or more C _1-6 alkyl groups. The alkyl groups may be the same or different).
R ^6b represents a C _1-6 alkyl group, a C _6-10 aryl group, or a (C _1-6 alkyl) (C _1-6 alkyl) amino group (provided that each of these has one or more halogens). In the case of having two or more halogens, the halogens may be the same or different, and the C _6-10 aryl group has one or more C _1-6 alkyl groups. And when having two or more C _1-6 alkyl groups, the alkyl groups may be the same or different).
R ^7b represents hydrogen or a C _1-6 alkyl group,
W ^b represents a C _1-6 alkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, or a C _1-6 alkylsulfonyl group (provided that these all have one or more halogens) In the case of having two or more halogens, the halogens may be the same or different. }
Any one of the groups represented by
Z ^b is halogen, cyano group, nitro group, phenyl group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, C _1-6 alkylthio group, C 1 Represents a _6-10 aryloxy group, a 5-6 membered heteroaryloxy group or a C _3-8 cycloalkyl group (provided that the C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group) , C _1-6 alkoxy group, and C _1-6 alkylthio group may have one or more halogens, and when having two or more halogens, the halogens may be the same or different. The phenyl group, C _6-10 aryloxy group, and 5- to 6-membered heteroaryloxy group are one or more selected from the group consisting of halogen, C _1-6 alkyl group and C _1-6 haloalkyl group. It may have a substituent, and when it has two or more substituents, the substitution The groups may be the same or different, and the C _3-8 cycloalkyl group may have one or more substituents selected from the group consisting of halogen and C _1-6 alkyl groups. When having the above substituents, the substituents may be the same or different, and when q represents an integer of 2 or more, Z ^b may be the same or different. Good.) ]
A cyclohexanone compound represented by:
[Item 5] n is an integer of 1 to 3,
R ^1b is hydrogen;
R ^2b and R ^3b are independently of each other hydrogen or a C _1-3 alkyl group (provided that when p is 2 or 3, two or three R ^2b may be the same or different. Well, 2 or 3 R ^3b may be the same or different.)
R ^4b is a phenyl group or 2-pyridyl group (provided that the phenyl group and 2-pyridyl group are halogen, C _1-3 alkyl group, C _1-3 alkoxy group, C _1-3 haloalkyl group, nitro group, It may have one or more substituents selected from the group consisting of a pentafluorothio group and a C _1-3 haloalkoxy group, and when it has two or more substituents, the substituents are the same. Or they may be different.)
G ^b is hydrogen or the following formula

{Wherein R ^5a represents a C _1-6 alkyl group, a C _6-10 aryl group, a C _1-6 alkoxy group, a C _3-6 alkenyloxy group, a C _3-6 alkynyloxy group or a C _6-10 aryloxy group. Represents a group,
W ^a represents ^a C _1-3 alkoxy group. }
Any of the groups represented by
The cyclohexanone compound according to [Item 4], wherein Z ^b is a C _1-3 alkyl group.
[Section 6] p is 2,
R ^2b and R ^3b are independently of each other hydrogen or a methyl group (provided that two R ^{2b s} may be the same or different, and two R ^{3b s} may be the same). May be different),
R ^4b is a phenyl group or a 2-pyridyl group (provided that the phenyl group and the 2-pyridyl group are one or more substituents selected from the group consisting of chlorine, fluorine, methyl group, methoxy group and trifluoromethyl group). Have)
G ^b is hydrogen, acetyl group, propionyl group, benzoyl group, methoxycarbonyl group, ethoxycarbonyl group, allyloxycarbonyl group, phenoxycarbonyl group, methoxymethyl group or ethoxymethyl group,
The cyclohexanone compound according to [Item 5], wherein Z ^b is a methyl group or an ethyl group.
[Claim 7] The cyclohexanone compound according to any one of [Claim 1] to [Claim 6], wherein G is hydrogen.
[Claim 8] A herbicide containing the cyclohexanone compound according to any one of [Claim 1] to [Claim 7] as an active ingredient.
[Claim 9] A method for controlling weeds, wherein an effective amount of the cyclohexanone compound according to any one of [Claim 1] to [Claim 7] is applied to weeds or soil where weeds grow.
[Item 10] Use of the cyclohexanone compound according to any one of [Item 1] to [Item 7] for controlling weeds.

  The compound of the present invention has an effect of controlling weeds and is effective as an active ingredient of a herbicide.

The substituent in the present invention will be described.
The C _1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms. For example, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, a sec-butyl group, a tert- Examples include a butyl group, a normal pentyl group, a sec-pentyl group, an isopentyl group, a neopentyl group, a normal hexyl group, and an isohexyl group.
The C _1-6 haloalkyl group means a C _1-6 alkyl group substituted with a halogen such as fluorine, chlorine, bromine, iodine, etc., for example, trifluoromethyl group, chloromethyl group, 2,2,2- Examples include trichloroethyl group, 2,2,2-trifluoroethyl group, and 2,2,2-trifluoro-1,1-dichloroethyl group.
The C _3-8 cycloalkyl group means a cycloalkyl group having 3 to 8 carbon atoms, and examples thereof include a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group.
The C _3-8 halocycloalkyl group means a cycloalkyl group having 3 to 8 carbon atoms substituted with a halogen such as fluorine, chlorine, bromine, iodine, etc., for example, a 2-chlorocyclopropyl group and 4,4 -A difluoro cyclohexyl group is mentioned.
(C _1-6 alkyl) C _3-8 cycloalkyl group means a cycloalkyl group having 3 to 8 carbon atoms substituted by an alkyl group having 1 to 6 carbon atoms, such as ethylcyclopropyl group, isobutyl A cyclopropyl group, 3-methylcyclopentyl group, and 4-methylcyclohexyl group are mentioned.
(C _3-8 cycloalkyl) C _1-6 alkyl group means a C _1-6 alkyl group substituted with a C _3-8 cycloalkyl group, such as a cyclopropylmethyl group and a cyclopentyl group. A methyl group is mentioned.
(C _3-8 cycloalkyl) The C _3-8 cycloalkyl group means a C _3-8 cycloalkyl group substituted by a C _3-8 cycloalkyl group. For example, 2-cyclopropylcyclo Examples include a propyl group and a 3-cyclopropylcyclopentyl group.
(C _3-8 halocycloalkyl) a C _1-6 alkyl group is a C _1-6 alkyl group substituted with a C _3-8 cycloalkyl group substituted with a halogen such as fluorine, chlorine, bromine or iodine. And includes, for example, a 2-chlorocyclopropylmethyl group and a 3-chlorocyclopentylethyl group.
{(C _1-6 alkyl) C _3-8 cycloalkyl} C _1-6 alkyl group is substituted with (a C _3-8 cycloalkyl group substituted with a C _1-6 alkyl). It means an alkyl group having 1 to 6 carbon atoms, and examples thereof include a 2-methylcyclopropylmethyl group and a 3-methylcyclopentylmethyl group.
The C _2-5 alkylene chain means an alkylene chain having 2 to 5 carbon atoms, and examples thereof include an ethylene chain, a propylene chain (trimethylene chain), a butylene chain (tetramethylene chain), and a pentylene chain (pentamethylene chain). .
When R ² and R ³ are bonded to an alkylene having 2 to 6 carbon atoms, R ² and R ^3, together with the carbon to which R ² and R ³ are attached, represent a cycloalkyl group having 3 to 6 carbon atoms . For example, when R ² and R ³ are combined to represent ethylene, it means cyclopropyl together with the carbon to which R ² and R ³ are bonded.
When R ^2b and R ^3b is bonded to an alkylene having 2 to 6 carbon atoms, and R ^2b and R ^3b, together with the carbon to which the R ^2b and R ^3b are attached, a cycloalkyl group having 3 to 6 carbon atoms Represent. For example, when R ^2b and R ^3b are combined to represent ethylene, it means cyclopropyl together with the carbon to which R ^2b and R ^3b are bonded.
The C _1-3 alkylidene group means an alkylidene group having 1 to 3 carbon atoms, and examples thereof include methylidene, ethylidene, and isopropylidene.

Examples of the halogen include fluorine, chlorine, bromine and iodine.
The C _2-6 alkenyl group means an alkenyl group having 2 to 6 carbon atoms, and examples thereof include a vinyl group, an allyl group, a 1-buten-3-yl group, and a 3-buten-1-yl group.
The C _2-6 alkynyl group means an alkynyl group having 2 to 6 carbon atoms, and examples thereof include an ethynyl group, a propargyl group, and a 2-butynyl group.
C _1-6 alkoxy group means an alkoxy group having 1 to 6 carbon atoms, such as methoxy group, ethoxy group, normal propyloxy group, isopropyloxy group, normal butoxy group, isobutoxy group, sec-butoxy group, Examples thereof include a tert-butoxy group, a normal pentyloxy group, a sec-pentyloxy group, an isopentyloxy group, a neopentyloxy group, a normal hexyloxy group, and an isohexyloxy group.
The C _1-6 alkylthio group means an alkylthio group having 1 to 6 carbon atoms, and examples thereof include a methylthio group, an ethylthio group, and an isopropylthio group.
The C _3-6 alkenyloxy group means an alkenyloxy group having 3 to 6 carbon atoms, and examples thereof include an allyloxy group and a 2-butenyloxy group.
The C _3-6 alkynyloxy group means an alkynyloxy group having 3 to 6 carbon atoms, and examples thereof include a propargyloxy group and a 2-butynyloxy group.
(C _6-10 aryl) C _1-6 alkoxy group means an alkoxy group having 1 to 6 carbon atoms substituted with an aryl group having 6 to 10 carbon atoms, such as a benzyloxy group and a phenethyloxy group. Is mentioned.
(C _6-10 aryl) C _1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms substituted with an aryl group having 6 to 10 carbon atoms, and examples thereof include a benzyl group and a phenethyl group. It is done.
The C _3-8 cycloalkoxy group means a C3-C8 cycloalkoxy group, and examples thereof include a cyclopropyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.
(C _1-6 alkyl) (C _1-6 alkyl) amino group means an amino group substituted with two identical or different alkyl groups having 1 to 6 carbon atoms, such as dimethylamino group, diethylamino group And an ethylmethylamino group.
(C _3-6 alkenyl) (C _3-6 alkenyl) amino group means an amino group substituted with two identical or different alkenyl groups having 3 to 6 carbon atoms, such as diallylamino group and di ( 3-butenyl) amino group.
(C _1-6 alkyl) (C _6-10 aryl) amino group means an amino group substituted with an alkyl group having 1 to 6 carbon atoms and a C _6-10 aryl group. For example, a methylphenylamino group And an ethylphenylamino group.
The C _1-6 alkylsulfinyl group means an alkylsulfinyl group having 1 to 6 carbon atoms, and examples thereof include a methylsulfinyl group, an ethylsulfinyl group, and an isopropylsulfinyl group.
The C _1-6 alkylsulfonyl group means an alkylsulfonyl group having 1 to 6 carbon atoms, and examples thereof include a methylsulfonyl group, an ethylsulfonyl group, and an isopropylsulfonyl group.
The C _6-10 aryl group means an aryl group having 6 to 10 carbon atoms, and examples thereof include a phenyl group and a naphthyl group.
The 5- to 6-membered heteroaryl group means an aromatic 5- or 6-membered heterocyclic group containing 1 to 3 heteroatoms selected from nitrogen, oxygen, and sulfur. For example, a 2-pyridyl group, Examples include 4-pyridyl group, 3-furyl group, pyrimidinyl group, 3-thienyl group and 1-pyrazolyl group.
The C _6-10 aryloxy group means an aryloxy group having 6 to 10 carbon atoms, and examples thereof include a phenoxy group and a naphthyloxy group.
The 5- to 6-membered heteroaryloxy group means an aromatic 5- or 6-membered heterocyclic oxy group containing 1 to 3 heteroatoms selected from nitrogen, oxygen, and sulfur. For example, 2-pyridyloxy Group, 3-pyridylroxy group.
The (C _1-6 alkoxy) carbonyl group means a carbonyl group substituted with an alkoxy group having 1 to 6 carbon atoms, and examples thereof include a methoxycarbonyl group and an ethoxycarbonyl group.
The (C _1-6 alkyl) amino group means an amino group substituted with an alkyl group having 1 to 6 carbon atoms, and examples thereof include a monomethylamino group and a monoethylamino group.
The (C _1-6 alkyl) aminocarbonyl group means an aminocarbonyl group substituted with an alkyl group having 1 to 6 carbon atoms, and examples thereof include a monomethylaminocarbonyl group and a monoethylaminocarbonyl group.
(C _1-6 alkyl) (C _1-6 alkyl) aminocarbonyl group means an aminocarbonyl group substituted with two identical or different alkyl groups having 1 to 6 carbon atoms, for example, dimethylaminocarbonyl group , Diethylaminocarbonyl group and ethylmethylaminocarbonyl group.
The (C _1-6 alkyl) carbonyl group means a carbonyl group substituted with an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methylcarbonyl group, an ethylcarbonyl group, and an isopropylcarbonyl group.
The C _6-10 arylthio group means an arylthio group having 6 to 10 carbon atoms, and examples thereof include a phenylthio group and a naphthylthio group.
The C _1-3 alkyl group means an alkyl group having 1 to 3 carbon atoms, and examples thereof include a methyl group, an ethyl group, a normal propyl group, and an isopropyl group.
The C _1-3 alkoxy group means an alkoxy group having 1 to 3 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a normal propyloxy group, and an isopropyloxy group.
The C _1-3 haloalkyl group means a C _1-3 alkyl group substituted with halogen such as fluorine, chlorine, bromine, iodine, etc., for example, trifluoromethyl group, chloromethyl group, 2,2,2- Examples include trichloroethyl group, 2,2,2-trifluoroethyl group, and 2,2,2-trifluoro-1,1-dichloroethyl group.
C _1-3 haloalkoxy group means an alkoxy group having 1 to 3 carbon atoms substituted with halogen such as fluorine, chlorine, bromine, iodine, etc., for example, trifluoromethoxy group, 2,2,2-trichloro Examples include an ethoxy group, a 3,3-difluoropropyloxy group, and a 2,2,2-trifluoroethoxy group.
The C _1-3 haloalkylthio group means a C _1-3 alkylthio group substituted with a halogen such as fluorine, chlorine, bromine, iodine, etc., for example, trifluoromethylthio group, chloromethylthio group, 2,2,2 -A trichloroethylthio group, a 2,2,2-trifluoroethylthio group and a 2,2,2-trifluoro-1,1-dichloroethylthio group are mentioned.

  In the compounds of the present invention, the cyclohexanone compounds represented by the formulas (I) and (II) may take the form of agriculturally acceptable salts with inorganic bases or organic bases. Also included are forms of cyclohexanone compounds. Examples of such salts include inorganic bases (eg, alkali metal (lithium, sodium, potassium, etc.) hydroxides, carbonates, hydrogen carbonates, acetates, hydrides, alkaline earth metals (magnesium, calcium, Hydroxide), hydride, etc., ammonia), organic bases (eg, dimethylamine, triethylamine, piperazine, pyrrolidine, piperidine, 2-phenylethylamine, benzylamine, ethanolamine, diethanolamine, pyridine, collidine, etc.), Examples thereof include salts formed by mixing with metal alkoxides (for example, sodium methoxide, potassium tert-butoxide, magnesium methoxide and the like).

When the compound of the present invention has one or more asymmetric centers, the compound has two or more stereoisomers (for example, enantiomers, diastereomers, etc.). The compound of the present invention includes all of these stereoisomers and a mixture of any two or more thereof.
When the compound of the present invention has geometric isomerism based on a double bond or the like, the compound contains two or more geometric isomers (for example, E / Z or trans / cis isomers, S-trans / S-cis). Each isomer) and the like. The compounds of the present invention include all of these geometric isomers and mixtures of any two or more thereof.

で示される部分が−Ｓ−ＣＨ₂ＣＨ₂−、−Ｓ−ＣＨ₂ＣＨ（ＣＨ₃）−、−Ｓ−ＣＨ（ＣＨ₃）ＣＨ₂−、−Ｏ−ＣＨ₂ＣＨ₂−、−ＣＨ₂−ＣＨ₂ＣＨ₂−、−Ｓ（Ｏ）−ＣＨ₂ＣＨ₂−、−Ｓ（Ｏ）−ＣＨ₂ＣＨ（ＣＨ₃）−、−Ｓ（Ｏ）₂−ＣＨ₂ＣＨ₂−、−Ｓ（Ｏ）₂−ＣＨ₂ＣＨ（ＣＨ₃）−、−Ｓ−ＣＨ₂Ｃ（ＣＨ₃）₂−、−Ｓ−ＣＨ₂Ｃ（シクロプロピル）−、−Ｓ−ＣＨ₂ＣＨ（Ｃ₂Ｈ₅）−、−Ｓ−ＣＨ₂−、−Ｓ−ＣＨ₂ＣＨ₂ＣＨ₂−、−Ｎ（ＣＨ₃）−ＣＨ₂ＣＨ（ＣＨ₃）−、又は−Ｎ（ＣＨ₃）−ＣＨ₂ＣＨ₂−である化合物；
Ｒ⁴がフェニル基、２−ピリジル基、３−ピリジル基、４−ピリジル基、２−ピリミジニル基、２−ピラジニル基、３−ピリダジニル基又は３−フリル基である化合物；
Ｚがフェニル基、又は、ハロゲンを有していてもよいＣ_1-6アルキル基である化合物； As an aspect of this invention compound, the following compounds are mentioned, for example.
a compound wherein m is 2;
a compound wherein n is 3;
a compound wherein m is 2 and n is 3;
A compound wherein X is S;
The compound wherein R ₂ is hydrogen;
The compound wherein R ₃ is hydrogen;
In formula (I)

In shown in part is _{-S-CH 2 CH 2 -,} - S-CH 2 CH (CH 3) -, - S-CH (CH 3) CH 2 -, - O-CH 2 CH 2 -, - CH 2 —CH ₂ CH ₂ —, —S (O) —CH ₂ CH ₂ —, —S (O) —CH ₂ CH (CH ₃ ) —, —S (O) ₂ —CH ₂ CH ₂ —, —S ( _{O) 2 -CH 2 CH (CH} 3) -, - S-CH 2 C (CH 3) 2 -, - S-CH 2 C ( _{cyclopropyl) -, - S-CH 2} CH (C 2 H 5) _{-, - S-CH 2 -} , - S-CH 2 CH 2 CH 2 -, - N (CH 3) -CH 2 CH (CH 3) -, or _{-N (CH 3) -CH 2 CH} 2 - in A compound;
A compound in which R ⁴ is a phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3-pyridazinyl group or 3-furyl group;
A compound in which Z is a phenyl group or a C _1-6 alkyl group _optionally having halogen;

｛式中、Ｌが酸素であり、
Ｒ⁵がＣ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_3-6アルケニルオキシ基、またはＣ_6-10アリールオキシ基であり、
Ｒ⁶がＣ_1-6アルキル基であり、
Ｒ⁷が水素であり、
ＷがＣ_1-6アルコキシ基である。｝
で表されるいずれかの基であり、
Ｚがハロゲン、フェニル基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、又は６員のヘテロアリールオキシ基であり（但し、該フェニル基、及び６員のヘテロアリールオキシ基はハロゲン、及びＣ_1-6ハロアルキル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。）。〕
で示されるシクロヘキサノン化合物。 m is an integer of 1, 2 or 3,
n is an integer of 1, 2, or 3;
X is CH _2, O, S, S (O), S (O) ₂ or N (CH ₃ );
R ¹ is hydrogen;
R ² and R ³ are each independently hydrogen or a C _1-6 alkyl group, or R ² and R ³ are bonded to form a C 2-6 alkenylene chain;
R ⁴ represents a C _6-10 aryl group or a 5-6 membered heteroaryl group (provided that the C _6-10 aryl group and the 5-6 membered heteroaryl group are halogen, cyano group, nitro group, pentafluoro It may have one or more substituents selected from the group consisting of a thio group, a C _1-6 alkyl group, and a C _1-6 alkoxy group, and when it has two or more substituents, The groups may be the same or different, and the C _1-6 alkyl group and the C _1-6 alkoxy group may have one or more halogens).
G is hydrogen or the following formula

{Wherein L is oxygen,
R ⁵ is a C _1-6 alkyl group, a C _1-6 alkoxy group, a C _3-6 alkenyloxy group, or a C _6-10 aryloxy group,
R ⁶ is a C _1-6 alkyl group,
R ⁷ is hydrogen;
W is a C _1-6 alkoxy group. }
Any of the groups represented by
Z is a halogen, a phenyl group, a C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, or a 6-membered heteroaryloxy group (provided that the phenyl group and 6-membered heteroaryl group) The aryloxy group may have one or more substituents selected from the group consisting of halogen and a C _1-6 haloalkyl group, and when having two or more substituents, the substituents are the same. Or it may be different.) ]
A cyclohexanone compound represented by:

［式中、
ｍは１、２又は３の整数を表し、
ｎは１〜５いずれかの整数を表し、
ＸはＣＨ₂、Ｏ、ＮＲ⁹、Ｓ、Ｓ（Ｏ）又はＳ（Ｏ）₂を表し、
Ｒ¹は水素またはメチル基を表し、
Ｒ²及びＲ³は、互いに独立に、水素、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_3-8ハロシクロアルキル基、（Ｃ_1-6アルキル）Ｃ_3-8シクロアルキル基、（Ｃ_3-8シクロアルキル）Ｃ_1-6アルキル基、（Ｃ_3-8シクロアルキル）Ｃ_3-8シクロアルキル基、（Ｃ_3-8ハロシクロアルキル）Ｃ_1-6アルキル基、｛（Ｃ_1-6アルキル）Ｃ_3-8シクロアルキル｝Ｃ_1-6アルキル基を表すか、Ｒ²とＲ³とが結合してＣ_2-5アルキレン鎖を表すか、又はＲ²とＲ³とが一緒になってハロゲンを有していてもよいＣ_1-3アルキリデン基を表し（但し、ｍが２又は３である場合、２又は３個のＲ²は同一であっても異なっていてもよく、２又は３個のＲ³は同一であっても異なっていてもよい。）、
Ｒ⁴はＣ_6-10アリール基又は５〜６員のヘテロアリール基を表し（但し、該Ｃ_6-10アリール基及び５〜６員のヘテロアリール基はハロゲン、シアノ基、ニトロ基、アミノ基、（Ｃ_1-6アルキル）アミノ基、（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノ基、ベンゾイルアミノ基、アミノカルボニル基、（Ｃ_1-6アルキル）アミノカルボニル基、（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノカルボニル基、ペンタフルオロチオ基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_3―6アルケニルオキシ基、Ｃ_3―6アルキニルオキシ基、Ｃ_6-10アリール基、Ｃ_6-10アリールオキシ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基、ヒドロキシカルボニル基、（Ｃ_1-6アルコキシ）カルボニル基及び（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基からなる群から選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。また、該（Ｃ_1-6アルキル）アミノ基、（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノ基、ベンゾイルアミノ基、（Ｃ_1-6アルキル）アミノカルボニル基、（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノカルボニル基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_3―6アルケニルオキシ基、Ｃ_3―6アルキニルオキシ基、Ｃ_6-10アリール基、Ｃ_6-10アリールオキシ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基、（Ｃ_1-6アルコキシ）カルボニル基及び（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。）、
Ｇは水素又は下記式

｛式中、Ｌは酸素またはイオウを表し、
Ｒ⁵はＣ_1-6アルキル基、Ｃ_3-8シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_6-10アリール基、（Ｃ_6-10アリール）Ｃ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_3-8シクロアルコキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基、（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノ基、（Ｃ_3-6アルケニル）（Ｃ_3-6アルケニル）アミノ基、（Ｃ_1-6アルキル）（Ｃ_6-10アリール）アミノ基又は５〜６員のヘテロアリール基を表し（但し、これらはいずれも１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。また、該Ｃ_3-8シクロアルキル基、Ｃ_6-10アリール基、（Ｃ_6-10アリール）Ｃ_1-6アルキル基のアリール部分、Ｃ_3-8シクロアルコキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基のアリール部分、（Ｃ_1-6アルキル）（Ｃ_6-10アリール）アミノ基のアリール部分及び５〜６員のヘテロアリール基はいずれも１以上のＣ_1-6アルキル基を有していてもよく、２以上のＣ_1-6アルキル基を有している場合、該アルキル基は同一であっても異なっていてもよい。）、
Ｒ⁶はＣ_1-6アルキル基、Ｃ_6-10アリール基又は（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノ基を表し(但し、これらはいずれも１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。また、該Ｃ_6-10アリール基は１以上のＣ_1-6アルキル基を有していてもよく、２以上のＣ_1-6アルキル基を有している場合、該アルキル基は同一であっても異なっていてもよい。)、
Ｒ⁷は水素又はＣ_1-6アルキル基を表し、
ＷはＣ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基を表す（但し、これらはいずれも１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。）。｝
で表されるいずれかの基を表し、
Ｒ⁹は、水素、Ｃ_1-6アルキル基、Ｃ_6-10アリール基、Ｃ_6-10アリールチオ基、Ｃ_6-10アリールスルフィニル基、Ｃ_6-10アリールスルホニル基を表し（但し、該Ｃ_1-6アルキル基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。該Ｃ_6-10アリール基、Ｃ_6-10アリールチオ基、Ｃ_6-10アリールスルフィニル基、Ｃ_6-10アリールスルホニル基は、ハロゲン、シアノ基、ニトロ基、アミノ基からなる群から選ばれる１以上の置換基を有していてもよい。）
Ｚはハロゲン、シアノ基、ニトロ基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、（Ｃ_1-6アルキル）カルボニル基、Ｃ_1-6アルキルチオ基、Ｃ_6-10アリールオキシ基、５〜６員のヘテロアリールオキシ基、Ｃ_3-8シクロアルキル基、Ｃ_6-10アリール基又は５〜６員のヘテロアリール基を表し、（但し、該Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、（Ｃ_1-6アルキル）カルボニル基、及びＣ_1-6アルキルチオ基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。該Ｃ_6-10アリール基、５〜６員のヘテロアリール基、Ｃ_6-10アリールオキシ基、及び５〜６員のヘテロアリールオキシ基はハロゲン、Ｃ_1-6アルキル基及びＣ_1-6ハロアルキル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。該Ｃ_3-8シクロアルキル基はハロゲン及びＣ_1-6アルキル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。さらに、ｎが２以上の整数を表わす場合、Ｚは同一であっても異なっていてもよい。）。〕
で示されるシクロヘキサノン化合物。 [1-1] Formula (I)

[Where:
m represents an integer of 1, 2 or 3,
n represents an integer of 1 to 5,
X represents CH ₂ , O, NR ⁹ , S, S (O) or S (O) ₂ ;
R ¹ represents hydrogen or a methyl group;
R ² and R ³ are independently of each other hydrogen, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, (C _1-6 alkyl) ) C _3-8 cycloalkyl group, (C _3-8 cycloalkyl) C _1-6 alkyl group, (C _3-8 cycloalkyl) C _3-8 cycloalkyl group, (C _3-8 halocycloalkyl) C _1-6 alkyl group, {(C _1-6 alkyl) C _3-8 cycloalkyl} represents a C _1-6 alkyl group, or R ² and R ³ combine to represent a C _2-5 alkylene chain Or R ² and R ³ together represent a C _1-3 alkylidene group which may have a halogen (provided that when m is 2 or 3, two or three R ² are the same) Or two or three R ^{3 s} may be the same or different).
R ⁴ represents a C _6-10 aryl group or a 5-6 membered heteroaryl group (provided that the C _6-10 aryl group and the 5-6 membered heteroaryl group are halogen, cyano group, nitro group, amino group) , (C _1-6 alkyl) amino group, (C _1-6 alkyl) (C _1-6 alkyl) amino group, benzoylamino group, aminocarbonyl group, (C _1-6 alkyl) aminocarbonyl group, (C _{1 -6} alkyl) (C _1-6 alkyl) aminocarbonyl group, pentafluorothio group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, C _{1 -6} alkylthio group, C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, C _6-10 aryl group, C _6-10 aryloxy group, C _1-6 alkylsulfinyl group, C _1-6 alkylsulfonyl group, hydroxycarbonyl group, (C _1-6 alkoxy) carboxamide May optionally have one or more substituents selected from Le group and (C _6-10 aryl) C _1-6 group consisting alkoxy group, and when two or more substituents, the substituents The (C _1-6 alkyl) amino group, (C _1-6 alkyl) (C _1-6 alkyl) amino group, benzoylamino group, (C ₁ -alkyl group), ₆ alkyl) aminocarbonyl group, (C _1-6 alkyl) (C _1-6 alkyl) aminocarbonyl group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 Alkoxy group, C _1-6 alkylthio group, C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, C _6-10 aryl group, C _6-10 aryloxy group, C _1-6 alkylsulfinyl group, C _1-6 alkylsulfonyl group, (C _1-6 alkoxy) carbonyl group, and (C _6-10 aryl) C _1-6 Al Alkoxy group may have one or more halogen atoms, and when two or more halogens, the halogens may be the same or different.),
G is hydrogen or the following formula

{Wherein L represents oxygen or sulfur,
R ⁵ is C _1-6 alkyl group, C _3-8 cycloalkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _6-10 aryl group, (C _6-10 aryl) C _1-6 Alkyl group, C _1-6 alkoxy group, C _3-8 cycloalkoxy group, C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 alkoxy group, (C _1-6 alkyl) (C _1-6 alkyl) amino group, (C _3-6 alkenyl) (C _3-6 alkenyl) amino group, (C _1-6 alkyl) (C _{6 -10} aryl) represents an amino group or a 5- to 6-membered heteroaryl group (provided that each of these may have one or more halogens, and when having two or more halogens, the halogen is it may be the same or different. Furthermore, the C _3-8 cycloalkyl group, C _6-10 aryl group, (C _6-10 aryl) C _1-6 a Aryl moiety of the kill group, C _3-8 cycloalkoxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 aryl moiety of alkoxy groups, (C _1-6 alkyl) (C _{6- 10} aryl) The aryl part of the amino group and the 5-6 membered heteroaryl group may each have one or more C _1-6 alkyl groups, and have two or more C _1-6 alkyl groups. The alkyl groups may be the same or different).
R ⁶ represents a C _1-6 alkyl group, a C _6-10 aryl group or a (C _1-6 alkyl) (C _1-6 alkyl) amino group (provided that each of these has one or more halogens) In the case of having two or more halogens, the halogens may be the same or different, and the C _6-10 aryl group has one or more C _1-6 alkyl groups. And when having two or more C _1-6 alkyl groups, the alkyl groups may be the same or different).
R ⁷ represents hydrogen or a C _1-6 alkyl group,
W represents a C _1-6 alkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, or a C _1-6 alkylsulfonyl group (provided that any of these may have one or more halogens) In the case of having two or more halogens, the halogens may be the same or different.) }
Any one of the groups represented by
R ⁹ represents hydrogen, a C _1-6 alkyl group, a C _6-10 aryl group, a C _6-10 arylthio group, a C _6-10 arylsulfinyl group, or a C _6-10 arylsulfonyl group (provided that the C _{1 -6} alkyl group may have one or more halogen atoms, and when two or more halogens, the halogens may be the same or different. the C _6-10 aryl group, The C _6-10 arylthio group, the C _6-10 arylsulfinyl group, and the C _6-10 arylsulfonyl group have one or more substituents selected from the group consisting of halogen, cyano group, nitro group, and amino group. May be good.)
Z is halogen, cyano group, nitro group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, (C _1-6 alkyl) carbonyl group, C _{1 -6} alkylthio group, C _6-10 aryloxy group, 5-6 membered heteroaryloxy group, C _3-8 cycloalkyl group, C _6-10 aryl group or 5-6 membered heteroaryl group; However, the C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, (C _1-6 alkyl) carbonyl group, and C _1-6 alkylthio group are 1 The halogen atom may be the same or different when it has two or more halogen atoms, the C _6-10 aryl group, a 5- to 6-membered hetero group. Aryl, C _6-10 aryloxy, and 5-6 membered heteroaryloxy groups are halogen, C _It may have one or more substituents selected from the group consisting of a _1-6 alkyl group and a C _1-6 haloalkyl group, and when it has two or more substituents, the substituents are the same. The C _3-8 cycloalkyl group may have one or more substituents selected from the group consisting of halogen and C _1-6 alkyl groups, and may have two or more substituents. And the substituents may be the same or different, and when n represents an integer of 2 or more, Z may be the same or different.) ]
A cyclohexanone compound represented by:

｛式中、Ｒ^5aはＣ_1-6アルキル基、Ｃ_6-10アリール基、Ｃ_1-6アルコキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基又はＣ_6-10アリールオキシ基を表し、
Ｒ^6aはＣ_1-6アルキル基を表し、
Ｗ^aはＣ_1-3アルコキシ基を表す。｝
で表されるいずれかの基であり、
Ｒ⁹が、水素、Ｃ_1-6アルキル基又はＣ_6-10アリールスルホニル基であり（但し、該Ｃ_1-6アルキル基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。該Ｃ_6-10アリールスルホニル基は、ハロゲン及びニトロ基からなる群から選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。）、
ＺがＣ_1-3アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-3アルコキシ基、Ｃ_3-8シクロアルキル基、ニトロ基、フェニル基又は５〜６員のヘテロアリールオキシ基（但し、該Ｃ_1-3アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-3アルコキシ基、フェニル基及び５〜６員のヘテロアリールオキシ基は、１以上のハロゲンを有していてもよく。２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。）である、前記［１−１］記載のシクロヘキサノン化合物。 [2-1] n is an integer of 1 to 3,
X represents CH ₂ , O, NR ⁹ , S, S (O) or S (O) ₂ ;
R ¹ is hydrogen;
R ² and R ³ are independently of each other hydrogen, a C _1-3 alkyl group, or R ² and R ³ are combined to form a C _2-5 alkylene chain (provided that when m is 2 or 3, 2 or 3 R ² may be the same or different, and 2 or 3 R ³ may be the same or different.)
R ⁴ is a phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3-pyridazinyl group or 3-furyl group (provided that the phenyl group, 2 -Pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3-pyridazinyl group and 3-furyl group are halogen, C _1-3 alkyl group, C _1-3 alkoxy group, C _1-3 haloalkyl group, C _1-3 alkylthio group, C _1-3 haloalkylthio group, cyano group, nitro group, amino group, pentafluorothio group, benzoylamino group and C _1-3 haloalkoxy group And when having two or more substituents, the substituents may be the same or different.)
G is hydrogen or the following formula

{Wherein R ^5a represents a C _1-6 alkyl group, a C _6-10 aryl group, a C _1-6 alkoxy group, a C _3-6 alkenyloxy group, a C _3-6 alkynyloxy group or a C _6-10 aryloxy group. Represents a group,
R ^6a represents a C _1-6 alkyl group,
W ^a represents ^a C _1-3 alkoxy group. }
Any of the groups represented by
R ⁹ is hydrogen, a C _1-6 alkyl group or a C _6-10 arylsulfonyl group (provided that the C _1-6 alkyl group may have one or more halogen atoms, and And the halogen may be the same or different, and the C _6-10 arylsulfonyl group has one or more substituents selected from the group consisting of halogen and nitro group. And when it has two or more substituents, the substituents may be the same or different).
Z is a C _1-3 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _1-3 alkoxy group, a C _3-8 cycloalkyl group, a nitro group, a phenyl group or a 5-6 membered hetero An aryloxy group (provided that the C _1-3 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-3 alkoxy group, phenyl group and 5- to 6-membered heteroaryloxy group are 1 The cyclohexanone compound according to the above [1-1], which may have the above-described halogen, or may have the same or different halogen when having two or more halogens. .

[3-1] m is 2,
X represents CH ₂ , O, NR ⁹ , S, S (O) or S (O) ₂ ;
R ² and R ³ are independently of each other hydrogen, methyl group, ethyl group, or R ² and R ³ are combined to form an ethylene chain (provided that two R ² are the same or different. And the two R ³ groups may be the same or different.)
R ⁴ is a phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3-pyridazinyl group or 3-furyl group (provided that the phenyl group, 2 -Pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3-pyridazinyl group and 3-furyl group are chlorine, bromine, iodine, fluorine, methyl group, methoxy group, nitro group , Amino group, cyano group, pentafluorothio group, pentafluoroethyl group, difluoroethyl group, heptafluoroisopropyl group, trifluoromethylthio group, benzoylamino group, trifluoromethoxy group and trifluoromethyl group One or more substituents).
G is hydrogen, acetyl group, propionyl group, butylcarbonyl group, benzoyl group, methylsulfonyl group, methoxycarbonyl group, ethoxycarbonyl group, allyloxycarbonyl group, phenoxycarbonyl group, methoxymethyl group or ethoxymethyl group,
R ⁹ is hydrogen, 2-nitrophenylsulfonyl group or methyl group,
Z is a methyl group, ethyl group, phenyl group, vinyl group, cyclopropyl group, nitro group, fluorine, chlorine, methoxy group, trifluoromethyl group, 5-trifluoromethyl-2-chloropyridyloxy group or ethynyl group The cyclohexanone compound according to [2-1] above.

［式中、
ｐは１、２又は３の整数を表し、
ｑは１〜５いずれかの整数を表し、
Ｘ^bはＣＨ₂、Ｏ、Ｓ、Ｓ（Ｏ）又はＳ（Ｏ）₂を表し、
Ｒ^1bは水素またはメチル基を表し、
Ｒ^2b及びＲ^3bは、互いに独立に、水素、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_3-8ハロシクロアルキル基、（Ｃ_1-6アルキル）Ｃ_3-8シクロアルキル基、（Ｃ_3-8シクロアルキル）Ｃ_1-6アルキル基、（Ｃ_3-8シクロアルキル）Ｃ_3-8シクロアルキル基、（Ｃ_3-8ハロシクロアルキル）Ｃ_1-6アルキル基、｛（Ｃ_1-6アルキル）Ｃ_3-8シクロアルキル｝Ｃ_1-6アルキル基を表すか、Ｒ^2bとＲ^3bとが結合してＣ_2-5アルキレン鎖を表すか、又はＲ^2bとＲ^3bとが一緒になってハロゲンを有していてもよいＣ_1-3アルキリデン基を表し（但し、ｐが２又は３である場合、２又は３個のＲ^2bは同一であっても異なっていてもよく、２又は３個のＲ^3bは同一であっても異なっていてもよい。）、
Ｒ^4bはＣ_6-10アリール基又は５〜６員のヘテロアリール基を表わし（但し、該Ｃ_6-10アリール基および５〜６員のヘテロアリール基はハロゲン、シアノ基、ニトロ基、ペンタフルオロチオ基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_3―6アルケニルオキシ基、Ｃ_3―6アルキニルオキシ基及び（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基からなる群から選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。また、該Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_3―6アルケニルオキシ基、Ｃ_3―6アルキニルオキシ基及び（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。）、
Ｇ^bは水素又は下記式

｛式中、Ｌ^bは酸素またはイオウを表し、
Ｒ^5bはＣ_1-6アルキル基、Ｃ_3-8シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_6-10アリール基、（Ｃ_6-10アリール）Ｃ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_3-8シクロアルコキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基、（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノ基、（Ｃ_3-6アルケニル）（Ｃ_3-6アルケニル）アミノ基、（Ｃ_1-6アルキル）（Ｃ_6-10アリール）アミノ基又は５〜６員のヘテロアリール基を表し（但し、これらはいずれも１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。また、該Ｃ_3-8シクロアルキル基、Ｃ_6-10アリール基、（Ｃ_6-10アリール）Ｃ_1-6アルキル基のアリール部分、Ｃ_3-8シクロアルコキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルコキシ基のアリール部分、（Ｃ_1-6アルキル）（Ｃ_6-10アリール）アミノ基のアリール部分及び５〜６員のヘテロアリール基はいずれも１以上のＣ_1-6アルキル基を有していてもよく、２以上のＣ_1-6アルキル基を有している場合、該アルキル基は同一であっても異なっていてもよい。）、
Ｒ^6bはＣ_1-6アルキル基、Ｃ_6-10アリール基又は（Ｃ_1-6アルキル）（Ｃ_1-6アルキル）アミノ基を表し(但し、これらはいずれも１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。また、該Ｃ_6-10アリール基は１以上のＣ_1-6アルキル基を有していてもよく、２以上のＣ_1-6アルキル基を有している場合、該アルキル基は同一であっても異なっていてもよい。)、
Ｒ^7bは水素又はＣ_1-6アルキル基を表し、
Ｗ^bはＣ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基を表す（但し、これらはいずれも１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。）。｝
で表されるいずれかの基を表し、
Ｚ^bはハロゲン、シアノ基、ニトロ基、フェニル基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_6-10アリールオキシ基、５〜６員のヘテロアリールオキシ基又はＣ_3-8シクロアルキル基を表す（但し、該Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、及びＣ_1-6アルキルチオ基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。該フェニル基、Ｃ_6-10アリールオキシ基、及び５〜６員のヘテロアリールオキシ基はハロゲン、Ｃ_1-6アルキル基及びＣ_1-6ハロアルキル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。該Ｃ_3-8シクロアルキル基はハロゲン及びＣ_1-6アルキル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。さらに、ｑが２以上の整数を表わす場合、Ｚ^bは同一であっても異なっていてもよい。）。〕
で示されるシクロヘキサノン化合物。 [4-1] Formula (II)

[Where:
p represents an integer of 1, 2 or 3,
q represents an integer of 1 to 5,
X ^b represents CH ₂ , O, S, S (O) or S (O) ₂ ;
R ^1b represents hydrogen or a methyl group,
R ^2b and R ^3b are independently of each other hydrogen, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, (C _1-6 alkyl) ) C _3-8 cycloalkyl group, (C _3-8 cycloalkyl) C _1-6 alkyl group, (C _3-8 cycloalkyl) C _3-8 cycloalkyl group, (C _3-8 halocycloalkyl) C _1-6 alkyl group, {(C _1-6 alkyl) C _3-8 cycloalkyl} represents a C _1-6 alkyl group, or R ^2b and R ^3b are combined to represent a C _2-5 alkylene chain Or R ^2b and R ^3b together represent a C _1-3 alkylidene group which may have a halogen (provided that when p is 2 or 3, 2 or 3 R ^2b are the same) Or two or three R ^3b may be the same or different.),
R ^4b represents a C _6-10 aryl group or a 5-6 membered heteroaryl group (provided that the C _6-10 aryl group and the 5-6 membered heteroaryl group are halogen, cyano group, nitro group, pentafluoro Thio group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, C _1-6 alkylthio group, C _3-6 alkenyloxy group, C _3-6 It may have one or more substituents selected from the group consisting of an alkynyloxy group and a (C _6-10 aryl) C _1-6 alkoxy group, and when it has two or more substituents, The groups may be the same or different, and the C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, C _1-6 alkylthio group , C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, and (C _6-10 aryl) C _1-6 Al Alkoxy group may have one or more halogen atoms, and when two or more halogens, the halogens may be the same or different.),
G ^b is hydrogen or the following formula

{Wherein L ^b represents oxygen or sulfur;
R ^5b is a C _1-6 alkyl group, C _3-8 cycloalkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _6-10 aryl group, (C _6-10 aryl) C _1-6 Alkyl group, C _1-6 alkoxy group, C _3-8 cycloalkoxy group, C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 alkoxy group, (C _1-6 alkyl) (C _1-6 alkyl) amino group, (C _3-6 alkenyl) (C _3-6 alkenyl) amino group, (C _1-6 alkyl) (C _{6 -10} aryl) represents an amino group or a 5- to 6-membered heteroaryl group (provided that each of these may have one or more halogens, and when having two or more halogens, the halogen is The C _3-8 cycloalkyl group, C _6-10 aryl group, (C _6-10 aryl) C _1-6 a may be the same or different. Aryl moiety of alkyl group, C _3-8 cycloalkoxy group, C _6-10 aryloxy group, aryl part of (C _6-10 aryl) C _1-6 alkoxy group, (C _1-6 alkyl) (C _{6- 10} aryl) The aryl part of the amino group and the 5-6 membered heteroaryl group may each have one or more C _1-6 alkyl groups, and have two or more C _1-6 alkyl groups. The alkyl groups may be the same or different).
R ^6b represents a C _1-6 alkyl group, a C _6-10 aryl group, or a (C _1-6 alkyl) (C _1-6 alkyl) amino group (provided that each of these has one or more halogens). In the case of having two or more halogens, the halogens may be the same or different, and the C _6-10 aryl group has one or more C _1-6 alkyl groups. And when having two or more C _1-6 alkyl groups, the alkyl groups may be the same or different).
R ^7b represents hydrogen or a C _1-6 alkyl group,
W ^b represents a C _1-6 alkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, or a C _1-6 alkylsulfonyl group (provided that these all have one or more halogens) In the case of having two or more halogens, the halogens may be the same or different. }
Any one of the groups represented by
Z ^b is halogen, cyano group, nitro group, phenyl group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, C _1-6 alkylthio group, C 1 Represents a _6-10 aryloxy group, a 5-6 membered heteroaryloxy group or a C _3-8 cycloalkyl group (provided that the C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group) , C _1-6 alkoxy group, and C _1-6 alkylthio group may have one or more halogens, and when having two or more halogens, the halogens may be the same or different. The phenyl group, C _6-10 aryloxy group, and 5- to 6-membered heteroaryloxy group are one or more selected from the group consisting of halogen, C _1-6 alkyl group and C _1-6 haloalkyl group. It may have a substituent, and when it has two or more substituents, the substitution The groups may be the same or different, and the C _3-8 cycloalkyl group may have one or more substituents selected from the group consisting of halogen and C _1-6 alkyl groups. When having the above substituents, the substituents may be the same or different, and when q represents an integer of 2 or more, Z ^b may be the same or different. Good.) ]
A cyclohexanone compound represented by:

｛式中、Ｒ^5aはＣ_1-6アルキル基、Ｃ_6-10アリール基、Ｃ_1-6アルコキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基又はＣ_6-10アリールオキシ基を表し、
Ｗ^aはＣ_1-3アルコキシ基を表す。｝
で表されるいずれかの基であり、
Ｚ^bがＣ_1-3アルキル基である、前記［４−１］記載のシクロヘキサノン化合物。 [5-1] n is an integer of 1 to 3,
R ^1b is hydrogen;
R ^2b and R ^3b are independently of each other hydrogen or a C _1-3 alkyl group (provided that when p is 2 or 3, two or three R ^2b may be the same or different. Well, 2 or 3 R ^3b may be the same or different.)
R ^4b is a phenyl group or 2-pyridyl group (provided that the phenyl group and 2-pyridyl group are halogen, C _1-3 alkyl group, C _1-3 alkoxy group, C _1-3 haloalkyl group, nitro group, It may have one or more substituents selected from the group consisting of a pentafluorothio group and a C _1-3 haloalkoxy group, and when it has two or more substituents, the substituents are the same. Or they may be different.)
G ^b is hydrogen or the following formula

{Wherein R ^5a represents a C _1-6 alkyl group, a C _6-10 aryl group, a C _1-6 alkoxy group, a C _3-6 alkenyloxy group, a C _3-6 alkynyloxy group or a C _6-10 aryloxy group. Represents a group,
W ^a represents ^a C _1-3 alkoxy group. }
Any of the groups represented by
The cyclohexanone compound according to [4-1], wherein Z ^b is a C _1-3 alkyl group.

[6-1] p is 2,
R ^2b and R ^3b are independently of each other hydrogen or a methyl group (provided that two R ^{2b s} may be the same or different, and two R ^{3b s} may be the same). May be different),
R ^4b is a phenyl group or a 2-pyridyl group (provided that the phenyl group and the 2-pyridyl group are one or more substituents selected from the group consisting of chlorine, fluorine, methyl group, methoxy group and trifluoromethyl group). Have)
G ^b is hydrogen, acetyl group, propionyl group, benzoyl group, methoxycarbonyl group, ethoxycarbonyl group, allyloxycarbonyl group, phenoxycarbonyl group, methoxymethyl group or ethoxymethyl group,
The cyclohexanone compound according to the above [5-1], wherein Z ^b is a methyl group or an ethyl group.

[7-1] The cyclohexanone compound according to any one of [1-1] to [6-1], in which G is hydrogen.

［式中、
ｍは１、２又は３の整数を表し、
ｎは１〜３いずれかの整数を表し、
ＸはＣＨ_2、Ｏ、ＮＲ⁹、Ｓ、Ｓ（Ｏ）又はＳ（Ｏ）₂を表し、
Ｒ¹は水素を表し、
Ｒ²及びＲ³は、互いに独立に、水素、Ｃ_1-6アルキル基を表すか、Ｒ²とＲ³とが結合してＣ_2-5アルキレン鎖を表し（但し、ｍが２又は３である場合、２又は３個のＲ²は同一であっても異なっていてもよく、２又は３個のＲ³は同一であっても異なっていてもよい。）、
Ｒ⁴はＣ_6-10アリール基又は５〜６員のヘテロアリール基を表し（但し、該Ｃ_6-10アリール基及び５〜６員のヘテロアリール基はハロゲン、シアノ基、ニトロ基、アミノ基、ベンゾイルアミノ基、ペンタフルオロチオ基、Ｃ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_6-10アリール基、ヒドロキシル基、（Ｃ_1-6アルキル）カルボニル基、及び（Ｃ_1-6アルコキシ）カルボニル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。また、該Ｃ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、及びＣ_6-10アリール基は、１以上のハロゲンまたは１以上のＣ_1-3ハロアルキル基を有していてもよく、２以上のハロゲンまたは２以上のＣ_1-3ハロアルキル基を有している場合、該ハロゲンまたはＣ_1-3ハロアルキル基は同一であっても異なっていてもよい。）、
Ｇは水素又は下記式

｛式中、Ｌは酸素を表し、
Ｒ⁵はＣ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_3-6アルケニルオキシ基、又はＣ_6-10アリールオキシ基を表し、
Ｒ⁶はＣ_1-6アルキル基を表し、
Ｒ⁷は水素を表し、
ＷはＣ_1-6アルコキシ基を表す。｝
で表されるいずれかの基を表し、
Ｒ⁹は、水素、Ｃ_1-6アルキル基、又はＣ_6-10アリールスルホニル基を表し（但し、該Ｃ_6-10アリールスルホニル基は１以上のニトロ基を有していてもよい。）
Ｚはハロゲン、ニトロ基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、５〜６員のヘテロアリールオキシ基、Ｃ_3-8シクロアルキル基、又はＣ_6-10アリール基を表し、（但し、該Ｃ_1-6アルキル基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。該５〜６員のヘテロアリールオキシ基はハロゲン、及びＣ_1-6ハロアルキル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。）。〕
で示されるシクロヘキサノン化合物。 [8-1] Formula (I)

[Where:
m represents an integer of 1, 2 or 3,
n represents an integer of 1 to 3,
X represents CH _2, O, NR ⁹ , S, S (O) or S (O) ₂ ;
R ¹ represents hydrogen,
R ² and R ³ each independently represent hydrogen, a C _1-6 alkyl group, or R ² and R ³ are bonded to each other to represent a C _2-5 alkylene chain (provided that m is 2 or 3). In some cases, 2 or 3 R ² may be the same or different, and 2 or 3 R ³ may be the same or different.)
R ⁴ represents a C _6-10 aryl group or a 5-6 membered heteroaryl group (provided that the C _6-10 aryl group and the 5-6 membered heteroaryl group are halogen, cyano group, nitro group, amino group) Benzoylamino group, pentafluorothio group, C _1-6 alkyl group, C _1-6 alkoxy group, C _1-6 alkylthio group, C _6-10 aryl group, hydroxyl group, (C _1-6 alkyl) carbonyl group And may have one or more substituents selected from the group consisting of (C _1-6 alkoxy) carbonyl groups, and when having two or more substituents, the substituents are the same. In addition, the C _1-6 alkyl group, C _1-6 alkoxy group, C _1-6 alkylthio group, and C _6-10 aryl group may be one or more halogens or one or more C _{1 -3} may have a haloalkyl group, 2 or more halogens or 2 or more If a C _1-3 haloalkyl group, the halogen or C _1-3 haloalkyl groups may be be the same or different.),
G is hydrogen or the following formula

{Wherein L represents oxygen,
R ⁵ represents a C _1-6 alkyl group, a C _1-6 alkoxy group, a C _3-6 alkenyloxy group, or a C _6-10 aryloxy group,
R ⁶ represents a C _1-6 alkyl group,
R ⁷ represents hydrogen,
W represents a C _1-6 alkoxy group. }
Any one of the groups represented by
R ⁹ represents hydrogen, a C _1-6 alkyl group, or a C _6-10 arylsulfonyl group (provided that the C _6-10 arylsulfonyl group may have one or more nitro groups).
Z is halogen, nitro group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, 5-6 membered heteroaryloxy group, C _3-8 cyclo _Represents an alkyl group or a C _6-10 aryl group (provided that the C _1-6 alkyl group may have one or more halogen atoms, and when the halogen atom has two or more halogen atoms, the halogen is The 5- to 6-membered heteroaryloxy group may have one or more substituents selected from the group consisting of halogen and a C _1-6 haloalkyl group, When it has two or more substituents, the substituents may be the same or different.) ]
A cyclohexanone compound represented by:

［式中、
ｍは１、２又は３の整数を表し、
ｎは１〜３いずれかの整数を表し、
ＸはＣＨ_2、Ｏ、ＮＲ⁹、Ｓ、Ｓ（Ｏ）又はＳ（Ｏ）₂を表し、
Ｒ¹は水素を表し、
Ｒ²及びＲ³は、互いに独立に、水素、Ｃ_1-6アルキル基を表すか、Ｒ²とＲ³とが結合してＣ_2-5アルキレン鎖を表し（但し、ｍが２又は３である場合、２又は３個のＲ²は同一であっても異なっていてもよく、２又は３個のＲ³は同一であっても異なっていてもよい。）、
Ｒ⁴はフェニル基、２−ピリジル基、３−ピリジル基、４−ピリジル基、２−ピリミジニル基、２−ピラジニル基、３−ピリダジニル基、１−ピラゾリル基、３−フリル基、２−チエニル基、２−チアゾリル基又は１，２，３−トリアゾリル基を表し（但し、該フェニル基、２−ピリジル基、３−ピリジル基、４−ピリジル基、２−ピリミジニル基、２−ピラジニル基、３−ピリダジニル基、１−ピラゾリル基、３−フリル基、２−チエニル基、２−チアゾリル基及び１，２，３−トリアゾリル基は、ハロゲン、シアノ基、ニトロ基、アミノ基、ベンゾイルアミノ基、ペンタフルオロチオ基、Ｃ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、フェニル基、ヒドロキシル基、（Ｃ_1-6アルキル）カルボニル基、及び（Ｃ_1-6アルコキシ）カルボニル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。また、該Ｃ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキルチオ基、及びフェニル基は、１以上のハロゲンまたは１以上のＣ_1-3ハロアルキル基を有していてもよく、２以上のハロゲンまたは２以上のＣ_1-3ハロアルキル基を有している場合、該ハロゲンまたはＣ_1-3ハロアルキル基は同一であっても異なっていてもよい。）、
Ｇは水素又は下記式

｛式中、Ｌは酸素を表し、
Ｒ⁵はＣ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_3-6アルケニルオキシ基、又は（フェノキシ基を表し、
Ｒ⁶はＣ_1-6アルキル基を表し、
Ｒ⁷は水素を表し、
ＷはＣ_1-6アルコキシ基を表す。｝
で表されるいずれかの基を表し、
Ｒ⁹は、水素、Ｃ_1-6アルキル基、又は２−ニトロフェニルスルホニル基を表し、
Ｚはハロゲン、ニトロ基、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6アルコキシ基、ピリジルオキシ基、Ｃ_3-8シクロアルキル基、又はフェニル基を表し、（但し、該Ｃ_1-6アルキル基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。該２−ピリジルオキシ基はハロゲン、及びＣ_1-6ハロアルキル基からなる群より選ばれる１以上の置換基を有していてもよく、２以上の置換基を有している場合、該置換基は同一であっても異なっていてもよい。）。〕
で示されるシクロヘキサノン化合物。 [9-1] Formula (I)

[Where:
m represents an integer of 1, 2 or 3,
n represents an integer of 1 to 3,
X represents CH _2, O, NR ⁹ , S, S (O) or S (O) ₂ ;
R ¹ represents hydrogen,
R ² and R ³ each independently represent hydrogen, a C _1-6 alkyl group, or R ² and R ³ are bonded to each other to represent a C _2-5 alkylene chain (provided that m is 2 or 3). In some cases, 2 or 3 R ² may be the same or different, and 2 or 3 R ³ may be the same or different.)
R ⁴ is a phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3-pyridazinyl group, 1-pyrazolyl group, 3-furyl group, 2-thienyl group. Represents a 2-thiazolyl group or a 1,2,3-triazolyl group (provided that the phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3- Pyridazinyl group, 1-pyrazolyl group, 3-furyl group, 2-thienyl group, 2-thiazolyl group and 1,2,3-triazolyl group are halogen, cyano group, nitro group, amino group, benzoylamino group, pentafluoro Thio group, C _1-6 alkyl group, C _1-6 alkoxy group, C _1-6 alkylthio group, phenyl group, hydroxyl group, (C _1-6 alkyl) carbonyl group, and (C _1-6 alkoxy) ) It may have one or more substituents selected from the group consisting of carbonyl groups, and when it has two or more substituents, the substituents may be the same or different. The C _1-6 alkyl group, C _1-6 alkoxy group, C _1-6 alkylthio group, and phenyl group may have one or more halogens or one or more C _1-3 haloalkyl groups, In the case of having two or more halogens or two or more C _1-3 haloalkyl groups, the halogens or C _1-3 haloalkyl groups may be the same or different).
G is hydrogen or the following formula

{Wherein L represents oxygen,
R ⁵ represents a C _1-6 alkyl group, a C _1-6 alkoxy group, a C _3-6 alkenyloxy group, or a (phenoxy group,
R ⁶ represents a C _1-6 alkyl group,
R ⁷ represents hydrogen,
W represents a C _1-6 alkoxy group. }
Any one of the groups represented by
R ⁹ represents hydrogen, a C _1-6 alkyl group, or a 2-nitrophenylsulfonyl group,
Z is halogen, nitro group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, pyridyloxy group, C _3-8 cycloalkyl group, or phenyl group (However, the C _1-6 alkyl group may have one or more halogens, and when it has two or more halogens, the halogens may be the same or different. The 2-pyridyloxy group may have one or more substituents selected from the group consisting of halogen and C _1-6 haloalkyl groups, and when it has two or more substituents, The groups can be the same or different.) ]
A cyclohexanone compound represented by:

  The herbicide of the present invention contains the compound of the present invention and an inert carrier. Examples of the inert carrier include a solid carrier, a liquid carrier, and a gas carrier. The herbicide of the present invention is usually further added with formulation adjuvants such as surfactants, sticking agents, dispersants, stabilizers, etc., wettable powder, wettable powder, flowable powder, granules, dry flowable powder, It is formulated into emulsions, aqueous liquids, oils, smokes, aerosols, microcapsules and the like. The herbicide of the present invention usually contains 0.1 to 80% by weight of the compound of the present invention.

Examples of the inert carrier include a solid carrier, a liquid carrier, and a gas carrier.
Examples of the solid carrier include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon, Examples of the liquid carrier include water, alcohols (for example, methanol, ethanol), ketones (for example, acetone, methyl ethyl ketone), aromatic carbonization, and the like. Hydrogens (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (eg, n-hexane, cyclohexane, kerosene), esters (eg, ethyl acetate, butyl acetate), nitriles (eg, , Acetonitrile, isobutylnitrile), ethers (eg Dioxane, diisopropyl ether), acid amides (e.g., N, N- dimethylformamide, dimethylacetamide), halogenated hydrocarbons (e.g., dichloroethane, trichlorethylene, and carbon tetrachloride), and the like.

  Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Etc.

  Other formulation adjuvants include, for example, fixing agents and dispersants, specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble high Molecules (for example, polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4) -Mixtures of methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or esters thereof.

The weed control method of the present invention includes a step of applying an effective amount of the compound of the present invention to weeds or soil where weeds grow. In the weed control method of the present invention, the herbicide of the present invention is usually used. Examples of the method of applying the herbicide of the present invention include a method of treating the herbicide of the present invention with foliage to weeds, a method of treating the herbicide of the present invention on the soil surface where weeds grow, and the herbicide of the present invention as a weed. The method of admixing to the soil where the rice grows can be mentioned. In the weed control method of the present invention, the compound of the present invention is usually used in an amount of 1 to 5000 g, preferably 10 to 1000 g per 10,000 m ^{2 of} area for controlling weeds.

The compound of the present invention can be used in farmland where the “plants” listed below are cultivated.
“Plants”: crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), lily family vegetables (eg, leek, onion, garlic, asparagus, etc.), celery family vegetables (carrot, parsley, celery, American redfish) Etc.), red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
Fruit trees: berries (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricot, prunes, etc.) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
Trees other than fruit trees: tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, snapdragon, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, blackfish, Japanese amberjack, moths, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.
Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, symbidium, begonia, etc.), biofuel plants (Jatropha, safflower, Amanas, switchgrass, miscanthus, kusayoshi, dangiku, kenaf, cassava, willow, etc.), houseplants, etc.

  The “plant” includes 5-hydroxyphenylpyruvate dioxygenase inhibitors such as isoxaflutole, acetolactate synthase (hereinafter abbreviated as ALS) inhibitors such as imazetapyr and thifensulfuronmethyl, and 5 glyphosate. -Enol pyruvyl shikimate-3-phosphate synthase (hereinafter abbreviated as EPSPS) inhibitor, glutamine synthetase inhibitor such as glufosinate, acetyl CoA carboxylase inhibitor such as cetoxidim, protoporphyrinogen oxidase inhibitor such as flumioxazin Plants to which resistance to auxinic herbicides such as herbicides, dicamba and 2,4-D, and herbicides such as bromoxynil have been imparted by classical breeding methods or genetic recombination techniques are also included.

Examples of “plants” tolerated by classical breeding methods include rapeseed, wheat, sunflower, rice and corn that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapy. Already sold under the brand name. Similarly, there are STS <(R)> soybeans that are resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl by classical breeding methods. Similarly, there is Express® sunflower resistant to ALS-inhibiting herbicides such as tribenuron methyl by classical breeding methods. Similarly, SR corn and the like are examples of crops to which tolerance has been imparted to acetyl CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods. Crops that have been rendered tolerant to acetyl CoA carboxylase inhibitors are Proc. Natl. Acad. Sci. USA, 87, 7175-7179 (1990).

Examples of “plants” that have been rendered resistant by genetic recombination techniques include glyphosate-resistant maize, soybean, cotton, rapeseed, and sugar beet varieties having EPSPS genes that are resistant to EPSPS inhibitors. RoundupReady <registered Have already been sold under trade names such as Trademark>, Agrisure <registered trademark> GT, Gly-Tol. Similarly, there are corn, soybean, cotton, and rapeseed varieties that are resistant to glufosinate by gene recombination technology, and are already sold under trade names such as LibertyLink (registered trademark). Similarly, bromoxynyl-resistant cotton by gene recombination technology is already sold under the trade name BXN. Similarly, there are corn and soybean varieties that are resistant to both glyphosate and ALS inhibitors, and the trade name of Optimum <(R)> GAT <(R)> has been published. In addition, the brand name of Cultivans (Cultivance (registered trademark)), a soybean variety resistant to imazapyr by genetic recombination technology, is disclosed.

Further, mutant acetyl CoA carboxylase resistant to acetyl CoA carboxylase inhibitors has been reported in Weed Science, 53, 728-746 (2005), etc., and such mutant acetyl CoA carboxylase gene can be transferred to plants by gene recombination technology. A plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing a mutation associated with introduction or resistance imparting into a crop acetyl-CoA carboxylase. Further, a base substitution mutation-introduced nucleic acid represented by chimera plastic technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.) Is introduced into plant cells, and plant acetyl-CoA carboxylase By introducing a site-specific amino acid substitution mutation into a gene or ALS gene, a plant resistant to an acetyl CoA carboxylase inhibitor or an ALS inhibitor can be produced.

In addition, a gene encoding a dicamba monooxygenase containing dicamba monooxygenase isolated from Pseudomonas maltophilia can be introduced to produce a crop such as soybean resistant to dicamba. (Behrens et al. 2007 Dicamba Resistance: Enlarging and Preserving Biotechnology-Based Weed Management Strategies. Science 316: 1185-1188).
Introducing a gene encoding aryloxyalkanoate dioxygenase, phenoxy herbicides such as 2,4-D, MCPA, dicloprop, mecoprop, pyridineoxyacetic acid systems such as fluroxypyr, triclopyr; Of aryloxyphenoxypropionic acid herbicides such as quizalofop-P-ethyl, haloxyhop-P-methyl, fluazihop-P-butyl, dicloholop, phenoxaprop-P-ethyl, metamihop, cyhalohop-butyl, clodinafop-propargyl, It is possible to produce crops that are resistant to both herbicide lines (WO2005 / 107437, WO2007 / 053482, WO2008 / 141154), D It is called HT crop.

Furthermore, a gene encoding HPPD showing resistance to an HPPD inhibitor can be introduced to produce a plant resistant to the HPPD inhibitor (US2004 / 0058427). Even if HPPD is inhibited by an HPPD inhibitor, a gene that can synthesize homogentisic acid, which is a product of HPPD, by another metabolic pathway is introduced, and as a result, a plant that is resistant to the HPPD inhibitor is created. (WO02 / 036787). A gene that overexpresses HPPD is introduced, and even in the presence of an HPPD inhibitor, HPPD is produced in an amount that does not affect the growth of the plant. As a result, a plant that is resistant to the HPPD inhibitor is produced. Can be produced (WO 96/38567). In addition to the introduction of a gene that overexpresses HPPD described above, a gene encoding prephenate dehydrogenase was introduced to increase the amount of p-hydroxyphenylpyruvic acid that is a substrate of HPPD, thereby inhibiting HPPD (Rippert P et.al. 2004 Engineering plant shikimate pathway for production of tocotriol and improvising herb.

The “plant” includes a plant imparted with resistance to nematodes and aphids by a classic breeding method. As an example, soybean introduced with a RAG1 (Resistance Aphid Gene 1) gene that imparts resistance to aphids can be mentioned.

The “plant” includes a plant which can synthesize, for example, a selective toxin known in the genus Bacillus using a gene recombination technique.
As toxins expressed in such genetically modified plants, insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; Cry1Ab, Cry1Ac and Cry1Ac derived from Bacillus thuringiensis , Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other delta-endotoxins, VIP1, VIP2, VIP3, VIP3A and other insecticidal proteins; nematode-derived insecticidal proteins; scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins Toxins produced by different animals; filamentous fungal toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors, patatin, Protease inhibitors such as tachin and papain inhibitors; ribosome inactivating proteins (RIP) such as lysine, corn-RIP, abrin, ruffin, saporin, bryodin; 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, Steroid metabolic enzymes such as cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; ion channel inhibitors such as sodium channel inhibitor and calcium channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; Chitinase; glucanase and the like.
Further, as toxins expressed in such genetically modified crops, δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab, VIP1, VIP2, VIP3 or VIPA, etc. Insecticidal protein hybrid toxins, partially defective toxins, and modified toxins are also included. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted. Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073, and the like. The toxins contained in these recombinant plants particularly confer resistance to Coleoptera pests, Diptera pests, and Lepidoptera pests.
In addition, genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known and some are commercially available. Examples of these genetically modified plants include YieldGard <(R)> (Corn variety expressing Cry1Ab toxin), YieldGard Rootworm <(R)> (Corn variety expressing Cry3Bb1 toxin), YieldGard Plus <(R)> (Cry1Ab and Cry3Bb1) Corn varieties expressing toxins), Herculex I <(R)> (corn varieties expressing phosphinothricin N-acetyltransferase (PAT) to confer resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B <(R)> ( Cotton varieties expressing Cry1Ac toxin), Bollgard I <(R)> (cotton varieties expressing Cry1Ac toxin), Bollgard II <(R)> (Cry1Ac and Cry Cotton varieties expressing Ab toxin), VIPCOT <(R)> (cotton varieties expressing VIP toxin), NewLeaf <(registered trademark) (potato varieties expressing Cry3A toxin), NatureGard <(R)>, Agrisure <(R) > GT Advantage (GA21 glyphosate resistant trait), Agurisure <(R)> CB Advantage (Bt11 corn borer (CB) trait), Protecta <(R)> and the like. In addition, there is a recombinant papaya variety into which a coat protein gene of papaya ring spot virus (PRSV) has been introduced, which has already been sold under the trade name of Rainbow Papaya (registered trademark).

The “plant” includes those imparted with an ability to produce an anti-pathogenic substance having a selective action using a gene recombination technique.
Examples of anti-pathogenic substances expressed in such genetically modified plants include, for example, sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.). Ion channel inhibitors; Stilbene synthase; Bibenzyl synthase; Chitinase; Glucanase; PR protein (PRPs, EP-A-0 392 225); Peptide antibiotics, antibiotics with heterocycles, protein factors involved in plant disease resistance And anti-pathogenic substances produced by microorganisms such as Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191, and the like.

The “plant” includes a plant imparted with resistance to environmental stresses such as cold resistance, heat resistance, drought resistance, salt resistance, etc. using a classic breeding method or a genetic recombination technique. Examples of crops to which drought resistance has been imparted include crops into which cspB has been introduced.

The “plant” also includes crops to which useful traits such as oil component modification and amino acid content enhancing traits have been imparted using genetic recombination techniques. Examples include VISTIVE <(R)> (low linolenic soybean with reduced linolenic content), high-lysine (high-oil) corn (corn with increased lysine or oil content), and the like.

Furthermore, the above-mentioned classic herbicide tolerance traits or useful traits such as herbicide tolerance genes, insecticidal pest resistance genes, antipathogenic substance production genes, environmental stress tolerance, oil component modification and amino acid content enhancement traits In addition, a stack variety combining a plurality of these is also included.

  The compound of the present invention can be mixed or used in combination with other insecticides, acaricides, nematicides, bactericides and / or synergists.

Examples of the active ingredient of such an insecticide include the following.
(1) Organophosphorus compound Acephate, Butathiofos, Chlorethoxyphos, Chlorfenvinfos, Chlorpyrifos, Chlorpyrifos-Methyl (Chlorpyrifos) , Diazinon, diclofenthion (ECP), dichlorvos (DDVP), dimethoate, dimethylvinphos, disulfoton, EPth, ethione Lofos, etrimfos, fenthion (MPP), phennitrothion (MEP), fothiazate, formothion, thoxathion, isoxathion, isoxathion, isoxathion (Mesulfofos), methidathion (DMTP), monocrotophos, monored (BRP), oxydeprofos (ESP), parathion, phosalone, phosmetone hosmet: PMP, pirimiphos-methyl, pyridafenthion, quinalphos, phentoate: PAP, profenofos, propiophos, propiophos, propofos (Salithion), sulprofos, tebupyrimfos, temefos, tetrachlorvinphos, terbufos, thiomethon, trichlorfon (trichon) lonpho: DEP), bamidithione, formate, kazusafos.

(2) Carbamate compounds alaniccarb, bendiocarb, benfurcarb, BPMC, carbaryl, carbofuran, carbothofen, lofocarb, lofocarb , Fenobucarb, phenothiocarb, phenoxycarb, furatiocarb, isoprocarb (MIPC), methocarb (metolcarb) hiocarb), oxamyl (oxamyl), pirimicarb (pirimicarb), propoxur (propoxur: PHC), XMC, thiodicarb (thiodicarb), xylylcarb (xylylcarb), aldicarb (aldicarb).

(3) Pyrethroid compounds Acrinathrin, allethrin, beta-cyfluthrin, bifenthrin, cycloprotorin, cyfluthrin, cyfluthrin, cyfluthrin, cyfluthrin, cyfluthrin ), Empentrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucitrate (fl) ucythrinate, flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praretrin, rmethrin. resmethrin), sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin. hrin), phenothrin, cyphenothrin, alpha-cypermethrin, zeta-permethrin, lambda cihalothrin (lambda-halothrin) ), Furamethrin, tau-fluvalinate, methfluthrin, profluthrin, dimethylfluthrin, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl 2 , 2-Dimethyl-3- (2-cyano-1-propyl) Propenyl) cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl 2,2,3,3-tetramethyl-cyclopropanecarboxylate, protrifenbute (Protrifenbute).

(4) Nereistoxin compound Cartap, bensultap, thiocyclam, monosultap, bisultap.

(5) Neonicotinoid compounds Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran (dinoteurin)

(6) Benzoylurea compounds Chlorfluazuron, bistrifluron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron (flufluxuron) hexafluuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron.

(7) Phenylpyrazole compound Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, pyrafluprole.

(8) Bt toxin Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof.

(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, tebufenozide.

(10) Organochlorine compounds Aldrin, dieldrin, chlordane, DDT, dienochlor, endosulfan, methoxychlor.

(11) Other insecticidal active ingredients machine oil, nicotine sulfate (nicotine-sulfate); avermectin (avermectin-B), bromopropyrate, buprofezin, chlorfenacyl (chlorophylline) ), DCIP (dichloropropionic ether), DD (1,3-Dichloropropene), emamectin benzoate, phenazaquin, flupyrazophos, tropurene, hydropyrene , Indoxacarb, methoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriprosulfur, inspiramide, spinomidol tolfenpyrad, triazamate, fulbenamide, flumectin, lepimectin, aluminum phosphide, arsenous oxide, benclothiaz (benclothiaz) Ium cyanamide, calcium polysulfide, DSP, flonicamid, flurimfen, formatenate, hydrogen phosphide, metam ammonium, metam ammonium, metam ammonium, metam ammonium Sodium (metham-sodium), methyl bromide, potassium oleate, spiromesifen, sulfoxafurol, sulfur, metaflumizone, metaflumizone Mat (spirotetrama) ), Pyrifluquinazon (pyrifluquinazone), spinetoram (spinetoram), chlorantraniliprole (chlorantraniliprole), Toraropiriru (tralopyril), diafenthiuron (diafenthiuron),

（式中、Ｘ^a1はメチル基、塩素、臭素又はフッ素を表し、Ｘ^a2はフッ素、塩素、臭素、Ｃ₁−Ｃ₄ハロアルキル基又はＣ₁−Ｃ₄ハロアルコキシ基を表し、Ｘ^a3はフッ素、塩素又は臭素を表し、Ｘ^a4は置換されていてもよいＣ₁−Ｃ₄アルキル、置換されていてもよいＣ₃−Ｃ₄アルケニル、置換されていてもよいＣ₃−Ｃ₄アルキニル、置換されていてもよいＣ₃−Ｃ₅シクロアルキルアルキル又は水素を表し、Ｘ^a5は水素又はメチル基を表し、Ｘ^a6は水素、フッ素又は塩素を表し、Ｘ^a7は水素、フッ素又は塩素を表す。）
で示される化合物、 Formula (A)

( ^Wherein X ^a1 represents a methyl group, chlorine, bromine or fluorine, X ^a2 represents a fluorine, chlorine, bromine, C ₁ -C ₄ haloalkyl group or C ₁ -C ₄ haloalkoxy group, and X ^a3 represents fluorine. Represents a chlorine or bromine, and X ^a4 is an ^optionally substituted C ₁ -C ₄ alkyl, an optionally substituted C ₃ -C ₄ alkenyl, an optionally substituted C ₃ -C ₄ alkynyl, a substituted C ₃ -C ₅ cycloalkylalkyl or hydrogen which may be ^substituted , X ^a5 represents hydrogen or a methyl group, X ^a6 represents hydrogen, fluorine or chlorine, and X ^a7 represents hydrogen, fluorine or chlorine. )
A compound represented by

（式中、Ｘ^b1はＸ^b2−ＮＨ−Ｃ（＝Ｏ）基、Ｘ^b2−Ｃ（＝Ｏ）−ＮＨ−ＣＨ₂基、Ｘ^b3−Ｓ（Ｏ）基、置換されていてもよいピロール−１−イル基、置換されていてもよいイミダゾール−１−イル基、置換されていてもよいピラゾール−１−イル基又は置換されていてもよい１，２，４−トリアゾール−１−イル基を表し、Ｘ^b2は２，２，２−トリフルオロエチル基等の置換されていてもよいＣ₁−Ｃ₄ハロアルキル基又はシクロプロピル基等の置換されていてもよいＣ₃−Ｃ₆シクロアルキル基を表し、Ｘ^b3はメチル等の置換されていてもよいＣ₁−Ｃ₄アルキル基を表し、Ｘ^b4は水素、塩素、シアノ基又はメチル基を表す。）で示される化合物、 Formula (B)

(In the formula, X ^b1 is X ^b2 —NH—C (═O) group, X ^b2 —C (═O) —NH—CH ₂ group, X ^b3 —S (O) group, optionally substituted pyrrole) -1-yl group, optionally substituted imidazol-1-yl group, optionally substituted pyrazol-1-yl group, or optionally substituted 1,2,4-triazol-1-yl group X ^b2 represents an optionally substituted C ₁ -C ₄ haloalkyl group such as a 2,2,2-trifluoroethyl group or an optionally substituted C ₃ -C ₆ cycloalkyl such as a cyclopropyl group. X ^b3 represents an ^optionally substituted C ₁ -C ₄ alkyl group such as methyl, and X ^b4 represents hydrogen, chlorine, a cyano group, or a methyl group.

（式中、Ｘ^c1は３，３，３−トリフルオロプロピル基等の置換されていてもよいＣ₁−Ｃ₄アルキル基、２，２，２−トリクロロエトキシ基等の置換されていてもよいＣ₁−Ｃ₄アルコキシ基、４−シアノフェニル基等の置換されていてもよいフェニル基又は２−クロロ−３−ピリジル基等の置換されていてもよいピリジル基を表し、Ｘ^c2はメチル基又はトリフルオロメチルチオ基を表し、Ｘ^c3はメチル基又はハロゲンを表す。）
で示される化合物。 Formula (C)

(In the formula, X ^c1 may be a substituted C ₁ -C ₄ alkyl group such as a 3,3,3-trifluoropropyl group or the like, a 2,2,2-trichloroethoxy group or the like. A C ₁ -C ₄ alkoxy group, a phenyl group which may be substituted such as 4-cyanophenyl group or a pyridyl group which may be substituted such as 2-chloro-3-pyridyl group, and X ^c2 is a methyl group Alternatively, it represents a trifluoromethylthio group, and X ^c3 represents a methyl group or a halogen.)
A compound represented by

Examples of the active ingredient of such an acaricide include the following.
Acequinocyl, amitraz, benzoximate, bifenazate, bromopropyrate, chinomethionate, BS chlorbenzylate clofenetine, cyflumethofen, kelsen (dicofol), etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate , Fluacrylpyrim, halfenprox, hexythiazodi, propargite tetrapene, fendipenti, pyridene, pyridene ), Spirodiclofen, spiromesifen, spirotetramat, amidoflumet, and cienopyrafen.

Examples of the active ingredient of such a nematicide include the following.
DCIP, fothiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartrate, and imicyafos.

Examples of the active ingredient of such a bactericide include the following.
(1) Polyhaloalkylthio compound captan, folpet, etc.
(2) Organophosphorus compounds IBP, EDDP, torquelofos-methyl and the like.
(3) Benzimidazole compound,
Benomyl, carbendazim, thiophanate-methyl, thiabendazole, etc.
(4) Carboxamide compounds Carboxin, mepronil, flutolanil, thifluzamide, furametopyr, boscalid, pentiopyrad, etc.
(5) Dicarboximide compound Procymidone, iprodione, vinclozolin, etc.
(6) Acylalanine compound metalaxyl, etc.
(7) Azole compounds Triadimefon, triadimenol, propiconazole, tebuconazole, cyproconazole, epoxiconol, and epoxiconazole ), Ipconazole, triflumizole, prochloraz, penconazole, flusilazole, dinicoazole, bromconazole, bromconazole, bromconazole, bromconazole Difenoconazole, metconazole, tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluconazole, fluconazole, fluconazole, fluconazole. tritonicazole, bittertanol, imazalil, flutriafol, etc.
(8) Morpholine compound Dodemorph, tridemorph, fenpropimorph, and the like.
(9) Strobilurin compounds azoxystrobin, cresoxime-methyl, methminostrobin, trifloxystrobin, picoxystrobin (picoxystrobin), cross Fluoxastrobin, dimoxystrobin, etc.
(10) Antibiotics Validamycin A, blastcidin S, kasugamycin, polyoxin and the like.
(11) Dithiocarbamate compounds Mancozeb, maneb, thiuram and the like.
(12) Other Bactericidal Active Ingredients Fthalide, Probenazole, Isoprothiolane, Tricyclazole, Pyroquilon, Ferimzone, olprozone carpropamid, diclocymet, phenoxanil, thiazinyl, diclomezine, teclophthalam, pencycuron, oxolinic acid, oxolinic acid, x Rifoline, fenpropidin, spiroxamine, fluazinam, iminooctadine, fenpiclonil, fludioxonimide, fludioxonimide, fludioxonimide , Silthiofam, proquinazide, cyflufenamide, basic copper calcium sulfate, dichlorofluanid, cyprodinil (cypropyridinyl) ethanil, mepanipyrim, dietofencarb, pyribencarb, famoxadone, fenamidone, fenamidone, fenamidone, fenamidone Valicarb (benthiavalicarb), cyazofamid (cyazofamid), mandipropamide (mandipropamid), metraphenone (metrafenone), fluopiram (fluopiram), bixafen (bixafen) and the like.

Examples of the active ingredient of such a synergist include the following.
Piperonyl butoxide, sesamex, sulfoxide, N- (2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-dicarboximide (MGK 264) N-decrimimidazole, WARF-antiresistant, TBPT, TPP, IBP, PSCP, methyl iodide (CH ₃ I), t-phenylbutenone Diethyl maleate, DMC, FDMC, ETP, and ETN.

Examples of the control target of the herbicide of the present invention include the following.
Crabgrass (Digitaria ciliaris), goosegrass (Eleusine indica), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), Kin foxtail (Setaria glauca), barnyardgrass (Echinochloa crus-galli), fall panicum (Panicum dichotomiflorum), Texas Pani cam (Panicum texanum), Meriken acne (Brachiaria platyphylla), Alexander glass (Braciaria plantagenea), Surinamegrass (Braciaria decumbens), Sebum sorghum (Sorghum halekeense) Emissions (Andropogon sorghum), bermudagrass (Cynodon dactylon), oats (Avena fatua), darnel (Lolium multiflorum), black grass (Alopecurus myosuroides), downy brome (Bromus tectorum), Arechinochahiki (Bromus sterilis), Hime canary grass (Phalaris minor) , Apera spica-venti, Poa annua, Agropyron repens, Cyperus iria, Cyperus rotundus, cymus , Pollula oleracea, Amaranthus retroflexus, Amaranthus hydritus, Amaranthus palm, Amaranthus palmeri, Anthus amuth spinosa), buckwheat (Fallopia convolvulus), sanaetade (Polygonum scabulum), American scorpiona (Persicaria pennsylvanica), hartade (Persicaria vulgaris), nagapumushi r Shi (Rumex obtusifolius), Japanese knotweed (Fallopia japonica), common lambsquarters (Chenopodium album), kochia (Kochia scoparia), knotweed (Polygonum longisetum), black nightshade (Solanum nigrum), white nosed Datura (Datura stramonium), Ipomoea purpurea (Ipomoea purpurea) , American morning glory (Ipomoea hederacea), Malmo American morning glory (Ipomoea hederacea var. integriuscula), beans morning glory (Ipomoea lacunosa), field bindweed (Convolvulus arvensis), Lamium purpureum (Lamium purpureum), henbit (Lamium amplexicaule), cocklebur (Xanthium pensylvanicum), wild sunflower (Helianthus annuus), Inukamitsure (Matricaria perforata or inodora), Chamomile (Matricaria chamomilla), corn marigold (Chrysanthemum segetum), orrasia (Matricaria matricariaides), ragweed (Ambrosia artemisiifo) ia), Ambrosia trifida (Ambrosia trifida), Erigeron canadensis (Erigeron canadensis), mugwort (Artemisia princeps), goldenrod (Solidago altissima), Erigeron bonariensis (Conyza bonariensis), the United States horn Aeschynomene indica (Sesbania exaltata), sicklepod (Cassia obtusifolia), Florida Bega Weed (Desmodium tortusum), White clover (Trifolium repens), Kudzu (Pueraria lobata), Caladium pea (Vicia angustifolia), Clover (Commelina communis) lina benghalensis), cleavers (Galium aparine), chickweed (Stellaria media), wild radish (Raphanus raphanistrum), Noharagarashi (Sinapis arvensis), shepherd's purse (Capsella bursa-pastoris), persian speedwell (Veronica persica), Veronica Hederifolia (Veronica hederifolia), field Pansy (Viola arvensis), Wild pansy (Viola tricolor), Papaver rhoeas, Forget-me-nots (Myosotis scorpioides), Otoweed (Asclepias syriaca) phorbia helioscopia), Euphorbia nutans (Chamaesyce nutans), the United States Fuuro (Geranium carolinianum), Netherlands Fuuro (Erodium cicutarium), horsetail (Equisetum arvense), Ashikaki (Leersia japonica), barnyardgrass (Echinochloa oryzicola), barnyardgrass (Echinochloa crus-galli var. formosensis), leptochloa chinensis (Leptochloa chinensis), smallflower umbrellaplant (Cyperus difformis), fimbristylis miliacea (Fimbristylis miliacea), Eleocharis acicularis (Eleocharis acicularis), Scirpus (Scirpus juncoides), Taiwan Yamai (Scirpus wallichii), Cyperus (Cyperus serotinus), water chestnut (Eleocharis kuroguwai ), Bobchochoenus koshevnikikovii, Shizunofectus nipponicus, Konogi (Mononochoria vaginalis), Azena (Lindernia procucu) bens), Abunome (Dopatrium junceum), Rotala indica (Rotala indica), Ammannia multiflora Roxb (Ammannia multiflora), Elatine triandra Schk (Elatine triandra), Choujitade (Ludwigia epilobioides), arrowhead (Sagittaria pygmaea), alisma canaliculatum (Alisma canaliculatum), Alismataceae (Sagittaria trifolia) , Potamogeton distinctus, Seri (Oenanthe javanica), Mizuhakobe (Callirichiche palustris), Azeto pepper (Lindernia mitrantha), American azena (Linder) ubia), Eclipta prostrata (Eclipta prostrata), Ibokusa (Murdannia keisak), Paspalum distichum (Paspalum distichum), Ezonosayanukagusa (Leersia oryzoides) weeds such as. Naganetera phyloxeroides, Frogsbit (Limnobium spongia), Waterfern (Salvinia spp.), Duckweed (Pistia stratiotes), Water pennywort (genus Hydrocotyle spp.) demersum), duckweed (genus Lemna), cabbage caroliniana, blackberry (Hydrilla verticillata), Southern naad (Najas guadalupensis), pondweet (Potamogeton) n illinoensis, etc. Potamogeton Pectinatus) Water meal (Wolffia genus), water mills foil such (Myriophyllum spicatum, Myriophyllum heterophyllum etc.), water hyacinth (Eichhornia crassipes) or the like aquatic plants. Mosses, moss, hornworts. Cyanobacteria. Ferns. Suckers of perennial crops (fruits, stones, berries, nuts, citrus, hops, grapes, etc.).

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｘ、ｎ、ｍ、Ｚは前記と同じ意味を表す。〕
本反応は通常溶媒中で行われる。使用できる溶媒としては、例えば、ベンゼン、トルエン、キシレン等の芳香族炭化水素類；ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；ジクロロメタン、クロロホルム、１，２−ジクロロエタン等のハロゲン化炭化水素類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；スルホラン等のスルホン類、又はこれらの混合溶媒が挙げられる。
本反応において用いられる塩基としては、例えば、トリエチルアミン、トリプロピルアミン、ピリジン、ジメチルアミノピリジン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基が挙げられる。該塩基の使用量は、式（２）で示される化合物に対して、通常１〜１０モル当量、好ましくは２〜５モル当量である。本反応に用いられる式（３）で示される化合物の使用量は、式（２）で示される化合物に対して、通常１〜３モル当量である。
本反応の反応温度は通常−６０〜１８０℃、好ましくは−１０〜１００℃である。本反応の反応時間は通常１０分〜３０時間である。
本反応の終了は、反応混合物の一部をサンプリングして、薄層クロマトグラフィー、高速液体クロマトグラフィー等の分析手段により確認することができる。本反応の終了後、例えば反応混合物に酸を添加して酸性とし、水と混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、式（１ａ）で示される化合物を得ることができる。 The compound of the present invention can be produced, for example, by the following production method.
Manufacturing method 1
Among the compounds of the present invention, a compound represented by the formula (1a) in which G is hydrogen is produced by reacting a compound represented by the formula (2) with a compound represented by the formula (3) in the presence of a base. be able to.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , X, n, m, Z represent the same meaning as described above. ]
This reaction is usually performed in a solvent. Examples of solvents that can be used include aromatic hydrocarbons such as benzene, toluene and xylene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran and dimethoxyethane; halogens such as dichloromethane, chloroform and 1,2-dichloroethane. Hydrocarbons; amides such as dimethylformamide and dimethylacetamide; sulfones such as sulfolane, or a mixed solvent thereof.
Examples of the base used in this reaction include organic bases such as triethylamine, tripropylamine, pyridine, dimethylaminopyridine, and 1,8-diazabicyclo [5.4.0] -7-undecene. The usage-amount of this base is 1-10 molar equivalent normally with respect to the compound shown by Formula (2), Preferably it is 2-5 molar equivalent. The usage-amount of the compound shown by Formula (3) used for this reaction is 1-3 mole equivalent normally with respect to the compound shown by Formula (2).
The reaction temperature of this reaction is usually −60 to 180 ° C., preferably −10 to 100 ° C. The reaction time for this reaction is usually 10 minutes to 30 hours.
The completion of this reaction can be confirmed by sampling a part of the reaction mixture and analyzing means such as thin layer chromatography or high performance liquid chromatography. After the completion of this reaction, for example, an acid is added to the reaction mixture to make it acidic, mixed with water, extracted with an organic solvent, and the resulting organic layer is dried, concentrated, and the like, The compound represented by 1a) can be obtained.

〔式中、Ｇ¹は式

（式中、Ｌ、Ｒ⁵、Ｒ⁶、Ｒ⁷およびＷは前記と同じ意味を表す。）
で表されるいずれかの基を表し、
Ｘ¹はハロゲン（例えば、塩素、臭素、ヨウ素等）又はハロゲンで置換されていてもよいＣ_1-3アルキルスルホニルオキシ基（例えば、メチルスルホニルオキシ基、トリフルオロメチルスルホニルオキシ基等）を表すか、式ＯＧ¹で表される基を表し（ただし、Ｇ¹が式

で表される基である場合、Ｘ¹はハロゲン又はハロゲンで置換されていてもよいＣ_1-3アルキルスルホニルオキシ基である。）、
Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｘ、ｎ、ｍ、Ｚは前記と同じ意味を表す。〕
本反応は溶媒中で行うことができる。使用できる溶媒としては、例えば、ベンゼン、トルエン等の芳香族炭化水素類；ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；ジクロロメタン、クロロホルム、１，２−ジクロロエタン等のハロゲン化炭化水素類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；ジメチルスルホキシド等のスルホキシド類；スルホラン等のスルホン類、又はこれらの混合溶媒が挙げられる。
本反応に用いられる式（４）で示される化合物としては、例えば、塩化アセチル、塩化プロピオニル、塩化イソブチリル、塩化ピバロイル、塩化ベンゾイル、シクロヘキサンカルボン酸クロリド等のカルボン酸のハロゲン化物；無水酢酸、無水トリフルオロ酢酸等のカルボン酸の無水物；クロロギ酸メチル、クロロギ酸エチル、クロロギ酸フェニル等の炭酸半エステルのハロゲン化物；塩化ジメチルカルバモイル等のカルバミン酸のハロゲン化物；塩化メタンスルホニル、塩化ｐ−トルエンスルホニル等のスルホン酸のハロゲン化物；メタンスルホン酸無水物、トリフルオロメタンスルホン酸無水物等のスルホン酸の無水物；クロロメチル メチル エーテル、エチル クロロメチル エーテル等のアルキル ハロゲノアルキル エーテル等が挙げられる。本反応に用いられる式（４）で示される化合物の使用量は、式（１ａ）で示される化合物に対して、通常１モル当量以上、好ましくは１〜３モル当量である。
本反応は通常、塩基の存在下に行われる。本反応において用いられる塩基としては、例えば、トリエチルアミン、トリプロピルアミン、ピリジン、ジメチルアミノピリジン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基；水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸カルシウム、水素化ナトリウム等の無機塩基が挙げられる。該塩基の使用量は、式（１a）で示される化合物に対して、通常０．５〜１０モル当量、好ましくは１〜５モル当量である。
本反応の反応温度は通常、−３０〜１８０℃、好ましくは−１０〜５０℃である。本反応の反応時間は通常、１０分〜３０時間である。
本反応の終了は、反応混合物の一部をサンプリングして、薄層クロマトグラフィー、高速液体クロマトグラフィー等の分析手段により確認することができる。本反応の終了後、例えば反応混合物と水とを混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、式（１ｂ）で示される化合物を得ることができる。
式（４）で示される化合物は公知の化合物であるか、あるいは公知の化合物から製造することができる。 Manufacturing method 2
The compound represented by the formula (1b) in which G is a group other than hydrogen among the compounds of the present invention can be produced from the compound represented by the formula (1a) and the compound represented by the formula G ¹ -X ¹ .

[Where G ¹ is the formula

(In the formula, L, R ⁵ , R ⁶ , R ⁷ and W represent the same meaning as described above.)
Any one of the groups represented by
X ¹ represents halogen (for example, chlorine, bromine, iodine, etc.) or a C _1-3 alkylsulfonyloxy group (for example, methylsulfonyloxy group, trifluoromethylsulfonyloxy group, etc.) optionally substituted with halogen. Represents a group represented by the formula OG ¹ (where G ¹ is a formula

X ¹ is a halogen or a C _1-3 alkylsulfonyloxy group which may be substituted with a halogen. ),
R ¹ , R ² , R ³ , R ⁴ , X, n, m and Z have the same meaning as described above. ]
This reaction can be carried out in a solvent. Examples of the solvent that can be used include aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; halogenated carbonization such as dichloromethane, chloroform, 1,2-dichloroethane, and the like. Examples thereof include hydrogens; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethylsulfoxide; sulfones such as sulfolane, or a mixed solvent thereof.
Examples of the compound represented by the formula (4) used in this reaction include halides of carboxylic acids such as acetyl chloride, propionyl chloride, isobutyryl chloride, pivaloyl chloride, benzoyl chloride, and cyclohexanecarboxylic acid chloride; Carboxylic acid anhydrides such as fluoroacetic acid; halides of carbonic acid half esters such as methyl chloroformate, ethyl chloroformate and phenyl chloroformate; halides of carbamic acid such as dimethylcarbamoyl chloride; methanesulfonyl chloride, p-toluenesulfonyl chloride Sulfonic acid halides such as methanesulfonic acid anhydride, trifluoromethanesulfonic acid anhydride, and the like; alkyl halogenoalkyl ethers such as chloromethyl methyl ether and ethyl chloromethyl ether That. The usage-amount of the compound shown by Formula (4) used for this reaction is 1 molar equivalent or more normally with respect to the compound shown by Formula (1a), Preferably it is 1-3 molar equivalent.
This reaction is usually performed in the presence of a base. Examples of the base used in this reaction include organic bases such as triethylamine, tripropylamine, pyridine, dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene; sodium hydroxide, hydroxide Examples include inorganic bases such as potassium, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, calcium carbonate, sodium hydride. The usage-amount of this base is 0.5-10 molar equivalent normally with respect to the compound shown by Formula (1a), Preferably it is 1-5 molar equivalent.
The reaction temperature of this reaction is usually −30 to 180 ° C., preferably −10 to 50 ° C. The reaction time for this reaction is usually 10 minutes to 30 hours.
The completion of this reaction can be confirmed by sampling a part of the reaction mixture and analyzing means such as thin layer chromatography or high performance liquid chromatography. After the completion of this reaction, for example, the reaction mixture and water are mixed, extracted with an organic solvent, and the resulting organic layer is dried and concentrated, whereby the compound represented by the formula (1b) is obtained. Can be obtained.
The compound represented by the formula (4) is a known compound or can be produced from a known compound.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｇ、ｎ、ｍ、Ｚは前記と同じ意味を表す。〕
該反応には酸化剤が用いられる。かかる酸化剤としては、例えば、過酸化水素；過酢酸、過安息香酸、ｍ−クロロ過安息香酸等の過酸類；メタ過ヨウ素酸ナトリウム、オゾン、二酸化セレン、クロム酸、四酸化二窒素、硝酸アセチル、ヨウ素、臭素、Ｎ−ブロモスクシンイミド、及びヨードシルベンゼンが挙げられる。酸化剤は式（１ｃ）で示される化合物１モルに対して通常０．８〜１．２モル用いられる。
該反応は、溶媒中で行われる。該反応に用いられる溶媒としては、例えば、ヘキサン、ヘプタン、オクタン、シクロヘキサン等の飽和炭化水素類；ベンゼン、トルエン、キシレン、クロロベンゼン、ジクロロベンゼン等の芳香族炭化水素類；ジクロロメタン、クロロホルム、１，２−ジクロロエタン、四塩化炭素等のハロゲン化飽和炭化水素類；メタノール、エタノール、プロパノール等のアルコール類；アセトニトリル等のニトリル類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；スルホラン等のスルホン類；酢酸、プロピオン酸等の有機酸類；水、及びこれらの混合物が挙げられる。
該反応の反応温度は、通常−５０〜１００℃、好ましくは０〜５０℃である。該反応の反応時間は通常１０分〜１０時間である。該反応の終了は、反応混合物の一部を薄層クロマトグラフィー、高速液体クロマトグラフィー等で分析することにより確認できる。該反応の終了後は、例えば反応混合物と水とを混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、式（１ｄ）で示される化合物を得ることができる。 Production method 3
Among the compounds of the present invention, a compound in which X is represented by S (O) can be produced by oxidizing a compound in which X is represented by S. When the portion other than X of the compound represented by the formula (1c) contains an alkylthio group, an alkylsulfinyl group, a haloalkylthio group and / or a haloalkylsulfinyl group, these groups may be oxidized.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , G, n, m, Z represent the same meaning as described above. ]
An oxidizing agent is used for the reaction. Examples of the oxidizing agent include hydrogen peroxide; peracids such as peracetic acid, perbenzoic acid, and m-chloroperbenzoic acid; sodium metaperiodate, ozone, selenium dioxide, chromic acid, dinitrogen tetroxide, and nitric acid. Acetyl, iodine, bromine, N-bromosuccinimide, and iodosylbenzene. The oxidizing agent is usually used in an amount of 0.8 to 1.2 mol per 1 mol of the compound represented by the formula (1c).
The reaction is performed in a solvent. Examples of the solvent used in the reaction include saturated hydrocarbons such as hexane, heptane, octane and cyclohexane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene; dichloromethane, chloroform, 1 and 2 -Halogenated saturated hydrocarbons such as dichloroethane and carbon tetrachloride; Alcohols such as methanol, ethanol and propanol; Nitriles such as acetonitrile; Amides such as dimethylformamide and dimethylacetamide; Sulfones such as sulfolane; Acetic acid and propion Organic acids such as acids; water, and mixtures thereof.
The reaction temperature is usually −50 to 100 ° C., preferably 0 to 50 ° C. The reaction time is usually 10 minutes to 10 hours. The completion of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like. After completion of the reaction, for example, the reaction mixture and water are mixed, extracted with an organic solvent, and the resulting organic layer is dried, concentrated, and the like, whereby the compound represented by the formula (1d) is obtained. Can be obtained.

〔式中、ｒは０または１の整数を表し、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｇ、ｎ、ｍ、Ｚは前記と同じ意味を表す。〕
該反応には酸化剤が用いられる。かかる酸化剤としては、例えば、過酸化水素；過酢酸、過安息香酸、ｍ−クロロ過安息香酸等の過酸類；メタ過ヨウ素酸ナトリウム、オゾン、二酸化セレン、クロム酸、四酸化二窒素、硝酸アセチル、ヨウ素、臭素、Ｎ−ブロモスクシンイミド、ヨードシルベンゼン、過酸化水素とタングステン触媒との組み合わせ、過酸化水素とバナジウム触媒との組み合わせ、及び過マンガン酸カリウムが挙げられる。、ｒが０である式（１ｅ）で示される化合物が用いられる場合、該酸化剤の使用量は該化合物１モル対して通常２〜１０モル、好ましくは２〜４モルである。また、ｒが１である式（１ｅ）で示される化合物が用いられる場合、該酸化剤の使用量は、該化合物１モルに対して通常１〜１０モル、好ましくは１〜３モルである。
該反応は、溶媒中で行われる。該反応に用いられる溶媒としては、例えば、ヘキサン、ヘプタン、オクタン、シクロヘキサン等の飽和炭化水素類；ベンゼン、トルエン、キシレン、クロロベンゼン、ジクロロベンゼン等の芳香族炭化水素類；ジクロロメタン、クロロホルム、１，２−ジクロロエタン、四塩化炭素等のハロゲン化飽和炭化水素類；メタノール、エタノール、プロパノール等のアルコール類；アセトニトリル等のニトリル類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；スルホラン等のスルホン類；酢酸、プロピオン酸等の有機酸類；水、及びこれらの混合物が挙げられる。
該反応の反応温度は、通常０〜２００℃、好ましくは２０〜１５０℃、である。該反応の反応時間は通常３０分〜１０時間である。該反応の終了は、反応混合物の一部を薄層クロマトグラフィー、高速液体クロマトグラフィー等で分析することにより確認できる。該反応の終了後は、例えば反応混合物と水とを混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、式（１ｆ）で示される化合物を得ることができる。 Manufacturing method 4
Among the compounds of the present invention, a compound in which X is represented by SO ₂ can be produced by oxidizing a compound in which X is represented by S or a compound represented by SO. When a group other than X of the compound represented by the formula (1e) contains an alkylthio group, an alkylsulfinyl group, a haloalkylthio group and / or a haloalkylsulfinyl group, these groups may be oxidized.

[Wherein, r represents an integer of 0 or 1, and R ¹ , R ² , R ³ , R ⁴ , G, n, m, and Z represent the same meaning as described above. ]
An oxidizing agent is used for the reaction. Examples of the oxidizing agent include hydrogen peroxide; peracids such as peracetic acid, perbenzoic acid, and m-chloroperbenzoic acid; sodium metaperiodate, ozone, selenium dioxide, chromic acid, dinitrogen tetroxide, and nitric acid. Examples include acetyl, iodine, bromine, N-bromosuccinimide, iodosylbenzene, a combination of hydrogen peroxide and a tungsten catalyst, a combination of hydrogen peroxide and a vanadium catalyst, and potassium permanganate. When the compound represented by the formula (1e) in which r is 0 is used, the amount of the oxidizing agent used is usually 2 to 10 mol, preferably 2 to 4 mol, relative to 1 mol of the compound. Moreover, when the compound shown by the formula (1e) whose r is 1 is used, the usage-amount of this oxidizing agent is 1-10 mol normally with respect to 1 mol of this compound, Preferably it is 1-3 mol.
The reaction is performed in a solvent. Examples of the solvent used in the reaction include saturated hydrocarbons such as hexane, heptane, octane and cyclohexane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene; dichloromethane, chloroform, 1 and 2 -Halogenated saturated hydrocarbons such as dichloroethane and carbon tetrachloride; Alcohols such as methanol, ethanol and propanol; Nitriles such as acetonitrile; Amides such as dimethylformamide and dimethylacetamide; Sulfones such as sulfolane; Acetic acid and propion Organic acids such as acids; water, and mixtures thereof.
The reaction temperature of the reaction is usually 0 to 200 ° C, preferably 20 to 150 ° C. The reaction time is usually 30 minutes to 10 hours. The completion of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like. After completion of the reaction, for example, the reaction mixture and water are mixed, extracted with an organic solvent, and the resulting organic layer is dried, concentrated, and the like, whereby the compound represented by the formula (1f) is obtained. Can be obtained.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｘ、ｎ、ｍ、Ｚは前記と同じ意味を表す。〕
該反応は通常溶媒中で行われる。使用できる溶媒としては、例えば、ベンゼン、トルエン、キシレン等の芳香族炭化水素類；ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；ジクロロメタン、クロロホルム、１，２−ジクロロエタン等のハロゲン化炭化水素類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；スルホラン等のスルホン類、又はこれらの混合溶媒が挙げられる。
反応に用いられる塩基としては、例えば、トリエチルアミン、トリプロピルアミン、ピリジン、ジメチルアミノピリジン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基が挙げられる。該塩基の使用量は、式（２）で示される化合物１モルに対して、通常１〜１０モル、好ましくは１〜５モルである。本反応で用いられる式（３１）で示される化合物の使用量は、式（２）で示される化合物１モルに対して、通常１〜３モルである。
該反応の反応温度は通常−６０〜１８０℃、好ましくは−１０〜１００℃である。該反応の反応時間は通常１０分〜３０時間である。
該反応の終了は、反応混合物の一部を薄層クロマトグラフィー、高速液体クロマトグラフィー等で分析することにより確認することができる。該反応終了後は、例えば反応混合物に酸を添加した後水と混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、式（１ａ）で示される化合物を得ることができる。 Manufacturing method 5
Among the compounds of the present invention, a compound represented by the formula (1a) in which G is hydrogen is produced by reacting a compound represented by the formula (2) with a compound represented by the formula (31) in the presence of a base. be able to.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , X, n, m, Z represent the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of solvents that can be used include aromatic hydrocarbons such as benzene, toluene and xylene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran and dimethoxyethane; halogens such as dichloromethane, chloroform and 1,2-dichloroethane. Hydrocarbons; amides such as dimethylformamide and dimethylacetamide; sulfones such as sulfolane, or a mixed solvent thereof.
Examples of the base used in the reaction include organic bases such as triethylamine, tripropylamine, pyridine, dimethylaminopyridine, and 1,8-diazabicyclo [5.4.0] -7-undecene. The usage-amount of this base is 1-10 mol normally with respect to 1 mol of compounds shown by Formula (2), Preferably it is 1-5 mol. The usage-amount of the compound shown by Formula (31) used by this reaction is 1-3 mol normally with respect to 1 mol of compounds shown by Formula (2).
The reaction temperature is usually −60 to 180 ° C., preferably −10 to 100 ° C. The reaction time is usually 10 minutes to 30 hours.
The completion of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like. After completion of the reaction, for example, by adding an acid to the reaction mixture, mixing with water, extracting with an organic solvent, and drying and concentrating the obtained organic layer, the formula (1a) The compounds shown can be obtained.

[式中、Ｇ³は式

（式中、Ｌ、Ｒ⁵は前記と同じ意味を表す。）
で表される基を表し、Ｇ⁴は水素もしくは式

（式中、Ｌ、Ｒ⁵は前記と同じ意味を表す。）
で表される基を表し、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、ｎ、ｍ、Ｚは前記と同じ意味を表す。〕
該反応は通常溶媒中で行われる。かかる溶媒としては、例えば、ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；ジクロロメタン、クロロホルム、１，２−ジクロロエタン等のハロゲン化炭化水素類、及びこれらの混合物が挙げられる。
ホスフィンとしては、例えばトリノルマルブチルホスフィン、トリフェニルホスフィンが挙げられる。該ホスフィンの使用量は、式（２２）で示される化合物に対して、通常１モル当量以上、好ましくは１〜３モル当量である。本反応で用いられる式（２１）で示される化合物の使用量は、式（２２）で示される化合物に対して、通常１モル当量以上、好ましくは１〜３モル当量である。
該反応の反応温度は通常−６０〜１８０℃、好ましくは−１０〜１００℃である。該反応の反応時間は通常１０分〜３０時間である。
該反応の終了は、反応混合物の一部を薄層クロマトグラフィー、高速液体クロマトグラフィー等で分析することにより確認することができる。該反応終了後は、例えば反応混合物に酸を添加した後水と混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、式（１ｇ）で示される化合物を得ることができる。 Manufacturing method 6
Among the compounds of the present invention, the compound represented by the formula (1g) can be produced by reacting the compound represented by the formula (22) with the compound represented by the formula (21) in the presence of phosphine.

[Where G ³ is the formula

(In the formula, L and R ⁵ have the same meaning as described above.)
G ⁴ represents hydrogen or a formula

(In the formula, L and R ⁵ have the same meaning as described above.)
Wherein R ¹ , R ² , R ³ , R ⁴ , n, m, and Z have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent include ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and mixtures thereof.
Examples of phosphine include trinormal butyl phosphine and triphenyl phosphine. The amount of the phosphine to be used is usually 1 molar equivalent or more, preferably 1 to 3 molar equivalents relative to the compound represented by the formula (22). The usage-amount of the compound shown by Formula (21) used by this reaction is 1 mol equivalent or more normally with respect to the compound shown by Formula (22), Preferably it is 1-3 mol equivalent.
The reaction temperature is usually −60 to 180 ° C., preferably −10 to 100 ° C. The reaction time is usually 10 minutes to 30 hours.
The completion of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like. After completion of the reaction, for example, by adding an acid to the reaction mixture, mixing with water, extracting with an organic solvent, and drying and concentrating the obtained organic layer, the formula (1 g) is obtained. The compounds shown can be obtained.

〔式中、
Ｒ¹⁰はＣ_1-6アルキル基、Ｃ_6-10アリール基(但し、Ｃ_1-6アルキル基、Ｃ_6-10アリール基は１以上のハロゲンを有していてもよく、２以上のハロゲンを有している場合、該ハロゲンは同一であっても異なっていてもよい。また、該Ｃ_6-10アリール基は１以上のＣ_1-6アルキル基を有していてもよく、２以上のＣ_1-6アルキル基を有している場合、該アルキル基は同一であっても異なっていてもよい。)、
Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、ｎ、ｍ、Ｚ、Ｇ³、Ｇ⁴は前記と同じ意味を表す。〕
該反応は通常溶媒中で行われる。かかる溶媒としては、例えば、ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；ジクロロメタン、クロロホルム、１，２−ジクロロエタン等のハロゲン化炭化水素類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類、及びこれらの混合物が挙げられる。本反応で用いられる式（１０）で示される化合物の使用量は、式（３４）で示される化合物に対して、通常１モル当量以上、好ましくは１〜５モル当量である。
該反応の反応温度は通常−６０〜１８０℃、好ましくは−１０〜１００℃である。該反応の反応時間は通常１０分〜３０時間である。
該反応の終了は、反応混合物の一部を薄層クロマトグラフィー、高速液体クロマトグラフィー等で分析することにより確認することができる。該反応の終了後は、例えば反応混合物に酸を添加した後水と混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、式（１ｇ）で示される化合物を得ることができる。 Manufacturing method 7
Among the compounds of the present invention, the compound represented by the formula (1g) can be produced by reacting the compound represented by the formula (34) with the compound represented by the formula (10).

[Where,
R ¹⁰ represents a C _1-6 alkyl group or a C _6-10 aryl group (provided that the C _1-6 alkyl group and the C _6-10 aryl group may have one or more halogen atoms, and The halogens may be the same or different, the C _6-10 aryl group may have one or more C _1-6 alkyl groups, and two or more In the case of having a C _1-6 alkyl group, the alkyl groups may be the same or different).
R ¹ , R ² , R ³ , R ⁴ , n, m, Z, G ³ and G ⁴ represent the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent include ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran and dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; amides such as dimethylformamide and dimethylacetamide. , And mixtures thereof. The usage-amount of the compound shown by Formula (10) used by this reaction is 1 molar equivalent or more normally with respect to the compound shown by Formula (34), Preferably it is 1-5 molar equivalent.
The reaction temperature is usually −60 to 180 ° C., preferably −10 to 100 ° C. The reaction time is usually 10 minutes to 30 hours.
The completion of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like. After completion of the reaction, for example, by adding an acid to the reaction mixture, mixing with water, extracting with an organic solvent, and drying and concentrating the obtained organic layer, the formula (1 g) is obtained. Can be obtained.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、ｎ、ｍ、Ｚ、Ｇ⁴は前記と同じ意味を表す。〕
該反応は通常溶媒中で行われる。かかる溶媒としては、例えば、ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；メタノール、エタノール等のアルコール類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類及びこれらの混合物が挙げられる。
反応に用いられる塩基としては、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、ナトリウムメトキシド、ナトリウムエトキシド等が挙げられる。該塩基の使用量は、式（１ｇ）で示される化合物１モルに対して、通常１〜１０モル、好ましくは１〜５モルである。
該反応の反応温度は通常−６０〜１８０℃、好ましくは−１０〜１００℃である。該反応の反応時間は通常１０分〜３０時間である。
該反応の終了は、反応混合物の一部を薄層クロマトグラフィー、高速液体クロマトグラフィー等で分析することにより確認することができる。該反応の終了後は、例えば反応混合物に酸を添加した後水と混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、式（１ｈ）で示される化合物を得ることができる。 Manufacturing method 8
Among the compounds of the present invention, the compound represented by the formula (1h) can be produced by hydrolyzing the compound represented by the formula (1g) in the presence of a base.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , n, m, Z, G ⁴ represent the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of such solvents include ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; alcohols such as methanol and ethanol; amides such as dimethylformamide and dimethylacetamide, and mixtures thereof.
Examples of the base used for the reaction include lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide and the like. The amount of the base to be used is generally 1 to 10 mol, preferably 1 to 5 mol, per 1 mol of the compound represented by the formula (1 g).
The reaction temperature is usually −60 to 180 ° C., preferably −10 to 100 ° C. The reaction time is usually 10 minutes to 30 hours.
The completion of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like. After completion of the reaction, for example, by adding an acid to the reaction mixture, mixing with water, extracting with an organic solvent, and drying and concentrating the obtained organic layer, formula (1h) Can be obtained.

〔式中、
Ｒ¹¹はＣ_6-10アリール基(但し、該Ｃ_6-10アリール基は、１以上のハロゲンまたは１以上のＣ_1-3ハロアルキル基を有していてもよく、２以上のハロゲンまたは２以上のＣ_1-3ハロアルキル基を有している場合、該ハロゲンまたはＣ_1-3ハロアルキル基は同一であっても異なっていてもよい。)を表し、
Ｒ¹、Ｒ²、Ｒ³、ｎ、ｍ、Ｚは前記と同じ意味を表す。〕
該反応は通常溶媒中で行われる。かかる溶媒としては、例えば、アセトニトリル等のニトリル類；ジメチルホルムアミド等のアミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。本反応で用いられる式（１１）で示される化合物の使用量は、式（３５）で示される化合物に対して、通常１〜１０モル当量であり、好ましくは１〜３モル当量である。本反応で用いられる硫酸銅の使用量は、式（３５）で示される化合物に対して、通常０．０２〜０．２モル当量である。本反応で用いられるアスコルビン酸ナトリウムの使用量は、式（３５）で示される化合物に対して、通常０．０５〜０．５モル当量である。
該反応の反応温度は通常、２０〜１００℃である。該反応の反応時間は通常１０分〜３０時間である。
該反応の終了は、反応混合物の一部を薄層クロマトグラフィー、高速液体クロマトグラフィー等で分析することにより確認することができる。該反応の終了後は、例えば反応混合物に酸を添加した後水と混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、式（１i）で示される化合物を得ることができる。
Manufacturing method 9
Among the compounds of the present invention, the compound represented by the formula (1i) is produced by reacting the compound represented by the formula (35) with the compound represented by the formula (11) in the presence of copper sulfate and sodium ascorbate. can do.

[Where,
R ¹¹ is a C _6-10 aryl group (provided that the C _6-10 aryl group may have one or more halogens or one or more C _1-3 haloalkyl groups, two or more halogens or two or more If a C _1-3 haloalkyl group, the halogen or C _1-3 haloalkyl group represents a good.) even though the same or different and
R ¹ , R ² , R ³ , n, m and Z have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of such solvents include nitriles such as acetonitrile; amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, and mixtures thereof. The usage-amount of the compound shown by Formula (11) used by this reaction is 1-10 molar equivalent normally with respect to the compound shown by Formula (35), Preferably it is 1-3 molar equivalent. The usage-amount of the copper sulfate used by this reaction is 0.02-0.2 molar equivalent normally with respect to the compound shown by Formula (35). The usage-amount of the sodium ascorbate used by this reaction is 0.05-0.5 molar equivalent normally with respect to the compound shown by Formula (35).
The reaction temperature is usually 20 to 100 ° C. The reaction time is usually 10 minutes to 30 hours.
The completion of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like. After completion of the reaction, for example, by adding an acid to the reaction mixture, mixing with water, extracting with an organic solvent, and drying and concentrating the obtained organic layer, the formula (1i) Can be obtained.

  Each compound produced by the above production methods 1 to 9 can be isolated and isolated by other known means such as concentration, vacuum concentration, extraction, phase transfer, crystallization, recrystallization, chromatography and the like. It may be possible to purify.

〔式中、Ｚ及びｎは前記と同じ意味を表す。〕
式（５）で示される化合物は公知の化合物であるか、あるいは公知の化合物から製造することができる。例えば、特開２００８−１３３２５２に記載されている方法、又はそれらに準じる方法に従い製造することができる。 Reference manufacturing method 1
The compound represented by the formula (3) is described in, for example, Marie-Luise Huber and John T. et al. According to the method described in Pinhey, Journal of Chemical Society Perkin Transition 1 (1990) 721, it can be produced by reacting the compound represented by the formula (5) with lead tetraacetate in the presence of a base.

[In formula, Z and n represent the same meaning as the above. ]
The compound represented by the formula (5) is a known compound or can be produced from a known compound. For example, it can be produced according to the method described in JP-A-2008-133252 or a method analogous thereto.

〔式中、Ｒ⁸はＣ_1-3アルキル基を示し、Ｘ、ｍ、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、及びｎは前記と同じ意味を表す。〕
式（２）で示される化合物は、例えば特開昭６３−１４６８５６に記載の方法に準じて製造することができる。
工程１において、式（９）で示される化合物と１−トリフェニルホスホラニリデン−２−プロパノンとのウィティッヒ反応により式（７）で示される化合物を製造することができる。
工程２において、式（７）で示される化合物を塩基性条件下、式（８）で示される化合物と反応させることにより式（６）で示される化合物を製造することができる。式（８）で示される化合物の中ではジメチルマロネート又はジエチルマロネートが好ましい。、本反応は適当な溶媒、例えばテトラヒドロフラン、メタノール、エタノール又はトルエンの中で実施される。
工程３において、式（６）で示される化合物を加水分解し、次に脱カルボン酸化することにより式（２）で示される化合物を製造することができる。
式（９）で示される化合物は公知の化合物であるか、あるいは公知の化合物から製造することができ、例えば、Ｔｅｔｒａｈｅｄｒｏｎ ｌｅｔｔｅｒ ２８（１９８７）２８９３−２８９４、Ｔｅｔｒａｈｅｄｒｏｎ ｌｅｔｔｅｒ ４７（２００６）５８６９−５８７３、Ｔｅｔｒａｈｅｄｒｏｎ ４２（１９８６）６０７１−６０９５、特開昭６３−１４６８５６に記載されている方法、又はそれらに準じる方法に従い製造することができる。 Reference production method 2
The compound represented by the formula (2) can be produced, for example, according to the following reaction scheme.

[Wherein R ⁸ represents a C _1-3 alkyl group, and X, m, R ¹ , R ² , R ³ , R ⁴ , and n represent the same meaning as described above. ]
The compound represented by the formula (2) can be produced, for example, according to the method described in JP-A No. 63-146856.
In Step 1, the compound represented by the formula (7) can be produced by a Wittig reaction between the compound represented by the formula (9) and 1-triphenylphosphoranylidene-2-propanone.
In Step 2, the compound represented by the formula (6) can be produced by reacting the compound represented by the formula (7) with the compound represented by the formula (8) under basic conditions. Among the compounds represented by the formula (8), dimethyl malonate or diethyl malonate is preferable. The reaction is carried out in a suitable solvent such as tetrahydrofuran, methanol, ethanol or toluene.
In the step 3, the compound represented by the formula (6) can be produced by hydrolyzing and then decarboxylating the compound represented by the formula (6).
The compound represented by the formula (9) is a known compound or can be produced from a known compound. For example, Tetrahedron letter 28 (1987) 2893-2894, Tetrahedron letter 47 (2006) 5869-5873, Tetrahedron 42 (1986) 6071-6095, JP-A 63-146856, or a method analogous thereto.

〔式中、Ｑはハロゲンを示し、Ｚ及びｎは前記と同じ意味を表す。〕
式（３１）で示される化合物は例えば、Ｂｕｌｌ．Ｃｈｅｍ．Ｓｏｃ．Ｊｐｎ．，６５，３５０４−３５０６（１９９２）に記載の方法に従って、式（３２）で示される化合物から製造することができる。
式（３２）で示される化合物は公知の化合物であるか、あるいは公知の化合物から製造することができ、例えば、ＷＯ２０１０１０２７６１、ＷＯ２００６０８４６６３に記載されている方法、又はそれらに準じる方法に従い製造することができる。 Reference manufacturing method 3
The compound represented by the formula (31) can be produced, for example, by the following method.

[In formula, Q shows a halogen and Z and n represent the same meaning as the above. ]
The compound represented by the formula (31) is described in, for example, Bull. Chem. Soc. Jpn. , 65, 3504-3506 (1992), from the compound represented by formula (32).
The compound represented by the formula (32) is a known compound, or can be produced from a known compound. For example, it can be produced according to the methods described in WO2010102761 and WO2006084643, or a method analogous thereto. .

〔式中、Ｇ²はベンジル基もしくはパラメトキシベンジル基を示し、Ｇ³、ｍ、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁸、Ｚ、Ｘ¹及びｎは前記と同じ意味を表す。〕
式（２５）で示される化合物は、例えば特開昭６３−１４６８５６に記載の方法に準じて製造することができる。
工程１
式（２７）で示される化合物は、式（２９）で示される化合物と１−トリフェニルホスホラニリデン−２−プロパノンとのウィティッヒ反応により製造することができる。
工程２
式（２６）で示される化合物は、式（２７）で示される化合物と式（８）で示される化合物とを塩基性条件下で反応させることにより製造することができる。
式（８）で示される化合物としては、例えばジメチルマロネート又はジエチルマロネートが挙げられる。反応に用いられる溶媒としては、例えばテトラヒドロフラン、メタノール、エタノール及びトルエンが挙げられる。
工程３
式（２５）で示される化合物は、式（２６）で示される化合物を加水分解した後脱炭酸により製造することができる。 Reference production example 4
The compound represented by the formula (22) can be produced, for example, by the following method.

[Wherein, G ² represents a benzyl group or a paramethoxybenzyl group, and G ³ , m, R ¹ , R ² , R ³ , R ⁸ , Z, X ¹ and n represent the same meaning as described above. ]
The compound represented by the formula (25) can be produced, for example, according to the method described in JP-A No. 63-146856.
Process 1
The compound represented by the formula (27) can be produced by a Wittig reaction between the compound represented by the formula (29) and 1-triphenylphosphoranylidene-2-propanone.
Process 2
The compound represented by formula (26) can be produced by reacting the compound represented by formula (27) with the compound represented by formula (8) under basic conditions.
Examples of the compound represented by the formula (8) include dimethyl malonate and diethyl malonate. Examples of the solvent used for the reaction include tetrahydrofuran, methanol, ethanol, and toluene.
Process 3
The compound represented by the formula (25) can be produced by decarboxylation after hydrolysis of the compound represented by the formula (26).

Process 4
The compound represented by the formula (24) can be produced by reacting the compound represented by the formula (25) with the compound represented by the formula (3) in the presence of a base.
The reaction is usually performed in a solvent.
Examples of such solvents include aromatic hydrocarbons such as benzene, toluene, and xylene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; halogenation such as dichloromethane, chloroform, 1,2-dichloroethane, and the like. Examples thereof include hydrocarbons; amides such as dimethylformamide and dimethylacetamide; sulfones such as sulfolane, and mixtures thereof.
Examples of the base used in the reaction include organic bases such as triethylamine, tripropylamine, pyridine, dimethylaminopyridine, and 1,8-diazabicyclo [5.4.0] -7-undecene. The amount of the base to be used is generally 1 to 10 mol, preferably 2 to 5 mol, per 1 mol of the compound represented by formula (25). The usage-amount of the compound shown by Formula (3) used by this reaction is 1-3 mol normally with respect to 1 mol of compounds shown by Formula (25). Reaction temperature of this reaction is -60-180 normally. ° C, preferably -10 to 100 ° C. The reaction time is usually 10 minutes to 30 hours.
The completion of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like. After completion of the reaction, for example, by adding an acid to the reaction mixture, mixing with water, extracting with an organic solvent, and drying and concentrating the obtained organic layer, formula (24) is performed. Can be obtained.

Process 5
The compound represented by the formula (23) can be produced by reacting the compound represented by the formula (24) with the compound represented by G ³ -X ¹ in the presence of a base. The reaction is usually performed in a solvent. Examples of the solvent include aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like. Amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane, and mixtures thereof.
Examples of the compound represented by the formula G ³ -X ¹ used in the reaction include halides of carboxylic acids such as acetyl chloride, propionyl chloride, isobutyryl chloride, pivaloyl chloride, benzoyl chloride, cyclohexanecarboxylic acid chloride; acetic anhydride, Carboxylic acid anhydrides such as trifluoroacetic anhydride; carbonates such as methyl chloroformate, ethyl chloroformate and phenyl chloroformate; halides of carbamic acid such as dimethylcarbamoyl chloride; methanesulfonyl chloride, p-toluene chloride Sulfonic acid halides such as sulfonyl; sulfonic acid anhydrides such as methanesulfonic anhydride and trifluoromethanesulfonic anhydride; alkyl halogenoalkyl ethers such as chloromethyl methyl ether and ethyl chloromethyl ether It is.
The amount of the compound represented by the formula G ³ -X ¹ used in the reaction is usually 1 mol or more, preferably 1 to 3 mol per 1 mol of the compound represented by the formula (24).
Examples of the base used in the reaction include organic bases such as triethylamine, tripropylamine, pyridine, dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene; sodium hydroxide, potassium hydroxide And inorganic bases such as calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, calcium carbonate, sodium hydride.
The amount of the base to be used is generally 0.5 to 10 mol, preferably 1 to 5 mol, per 1 mol of the compound represented by the formula (24).
The reaction temperature of the reaction is usually -30 to 180 ° C, preferably -10 to 50 ° C. The reaction time is usually 10 minutes to 30 hours.
The completion of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like. After completion of the reaction, for example, the reaction mixture and water are mixed, extracted with an organic solvent, and the resulting organic layer is dried, concentrated, and the like, thereby performing the compound represented by the formula (23). Can be obtained.
The compound represented by the formula G ³ -X ¹ is a known compound or can be prepared from a known compound.

Step 6
The compound represented by the formula (22) can be produced by reacting the compound represented by the formula (23) in the presence of a metal.
The reaction is usually performed in a solvent. Examples of the solvent include aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; alcohols such as methanol and ethanol; esters such as ethyl acetate and the like. Of the mixture.
Examples of the metal used in the reaction include palladium and platinum. The amount of metal used in the reaction is usually 0.01 mol or more, preferably 0.01 to 0.5 mol, relative to 1 mol of the compound represented by the formula (23).
The reaction temperature of the reaction is usually -30 to 180 ° C, preferably -10 to 50 ° C. The reaction time is usually 10 minutes to 30 hours.
The completion of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like. After completion of the reaction, for example, the compound represented by the formula (22) can be obtained by performing an operation such as filtering the reaction mixture through Celite (registered trademark) and concentrating the obtained liquid under reduced pressure.

〔式中、Ｒ¹⁰、Ｘ¹、Ｒ¹、Ｒ²、Ｒ³、ｎ、ｍ、Ｇ³、Ｚは前記と同じ意味を表す。〕
該反応は通常溶媒中で行われる。かかる溶媒としては、例えば、ベンゼン、トルエン等の芳香族炭化水素類；ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；ジクロロメタン、クロロホルム、１，２−ジクロロエタン等のハロゲン化炭化水素類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；ジメチルスルホキシド等のスルホキシド類；スルホラン等のスルホン類、及びこれらの混合物が挙げられる。
該反応に用いられる式（３５）で示される化合物としては、例えば、塩化メタンスルホニル、塩化ｐ−トルエンスルホニル等のスルホン酸のハロゲン化物；メタンスルホン酸無水物、トリフルオロメタンスルホン酸無水物等のスルホン酸無水物が挙げれる。該反応に用いられる式（３５）で示される化合物の使用量は、式（２２）で示される化合物１モルに対して、通常１モル以上、好ましくは１〜３モルである。
該反応は通常、塩基の存在下に行われる。本反応で用いられる塩基としては、例えば、トリエチルアミン、トリプロピルアミン、ピリジン、ジメチルアミノピリジン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基；水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸カルシウム、水素化ナトリウム等の無機塩基が挙げられる。該塩基の使用量は、式（２２）で示される化合物１モルに対して、通常０．５〜１０モル、好ましくは１〜５モルである。
該反応の反応温度は通常、−３０〜１８０℃、好ましくは−１０〜５０℃である。該反応の反応時間は通常、１０分〜３０時間である。
該反応の終了は、反応混合物の一部を薄層クロマトグラフィー、高速液体クロマトグラフィー等で分析することにより確認することができる。
該反応の終了後は、例えば反応混合物と水とを混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、式（３４）で示される化合物を得ることができる。
式（３５）で示される化合物は公知の化合物であるか、あるいは公知の化合物から製造することができる。 Reference production example 5
The compound represented by the formula (34) can be produced by reacting the compound represented by the formula (22) with the compound represented by the formula (35).

[Wherein, R ¹⁰ , X ¹ , R ¹ , R ² , R ³ , n, m, G ³ , Z represent the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent include aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like. Amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane, and mixtures thereof.
Examples of the compound represented by the formula (35) used in the reaction include halides of sulfonic acids such as methanesulfonyl chloride and p-toluenesulfonyl chloride; sulfones such as methanesulfonic anhydride and trifluoromethanesulfonic anhydride. An acid anhydride is mentioned. The usage-amount of the compound shown by Formula (35) used for this reaction is 1 mol or more normally with respect to 1 mol of compounds shown by Formula (22), Preferably it is 1-3 mol.
The reaction is usually performed in the presence of a base. Examples of the base used in this reaction include organic bases such as triethylamine, tripropylamine, pyridine, dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene; sodium hydroxide, hydroxide Examples include inorganic bases such as potassium, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, calcium carbonate, sodium hydride. The amount of the base to be used is generally 0.5 to 10 mol, preferably 1 to 5 mol, per 1 mol of the compound represented by the formula (22).
The reaction temperature of the reaction is usually -30 to 180 ° C, preferably -10 to 50 ° C. The reaction time is usually 10 minutes to 30 hours.
The completion of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like.
After completion of the reaction, for example, the reaction mixture and water are mixed, extracted with an organic solvent, and the resulting organic layer is dried, concentrated, and the like, whereby the compound represented by the formula (34) is obtained. Can be obtained.
The compound represented by the formula (35) is a known compound or can be produced from a known compound.

〔式中、Ｒ¹⁰、Ｒ¹、Ｒ²、Ｒ³、Ｇ³、ｎ、ｍ、Ｚは前記と同じ意味を表す。〕
該反応は通常溶媒中で行われる。かかる溶媒としては、例えば、ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。本反応で用いられるアジ化ナトリウムの使用量は、式（３４−a）で示される化合物１モルに対して、通常１〜２０モル当量であり、好ましくは２〜１０モル当量である。本反応で用いられる１５−クラウン５−エーテルの使用量は、式（３４−a）で示される化合物１モルに対して、通常０．０２〜０。２モル当量である。
該反応の反応温度は好ましくは−１０〜１２０℃である。該反応の反応時間は通常、１０分〜３０時間である。
該反応の終了は、反応混合物の一部を薄層クロマトグラフィー、高速液体クロマトグラフィー等で分析することにより確認することができる。
該反応の終了後は、例えば反応混合物を濃縮することにより式（３５）で示される化合物を得ることができる。
式（３４−ａ）で示される化合物は例えば参考製造例５に記載の方法で製造することができる。
Reference production example 6
The compound represented by the formula (35) can be produced by reacting the compound represented by the formula (34-a) with sodium azide in the presence of 15-crown 5-ether.

[Wherein, R ¹⁰ , R ¹ , R ² , R ³ , G ³ , n, m, and Z represent the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent include amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide and mixtures thereof. The usage-amount of the sodium azide used by this reaction is 1-20 molar equivalent normally with respect to 1 mol of compounds shown by Formula (34-a), Preferably it is 2-10 molar equivalent. The usage-amount of 15-crown 5-ether used by this reaction is 0.02-0.2 molar equivalent normally with respect to 1 mol of compounds shown by Formula (34-a).
The reaction temperature of the reaction is preferably −10 to 120 ° C. The reaction time is usually 10 minutes to 30 hours.
The completion of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like.
After completion of the reaction, for example, the compound represented by the formula (35) can be obtained by concentrating the reaction mixture.
The compound represented by the formula (34-a) can be produced, for example, by the method described in Reference Production Example 5.

  Some of the compounds of the present invention that can be produced by the above production method are shown below.

Hereinafter, the present invention will be described more specifically with reference to production examples, reference examples, formulation examples, and test examples, but the present invention is not limited to these examples.
In Production Examples and Reference Examples, room temperature usually indicates 10 to 30 ° C. ¹ H NMR represents a proton nuclear magnetic resonance spectrum, tetramethylsilane was used as an internal standard, and chemical shift (δ) was expressed in ppm.
The symbols used in the production examples and reference examples have the following meanings.
CDCl ₃ : deuterated chloroform, s: singlet, d: doublet, t: triplet, q: quartet, brs: wide singlet, m: multiplet, J: coupling constant, Me: methyl group, Et: ethyl group, Phe: Phenyl group, OMe: methoxy group, OAc: acetoxy group, Pyr: pyridyl group, Bn: benzyl group, Ts: p-toluenesulfonyl group.

室温にて、式（１０−１）で示される化合物１０ｇおよびテトラヒドロフラン１５ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこに９５％アクロレイン４．０ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水洗し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−１）で示される化合物１８．１ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．７７（１Ｈ，ｓ），７．５１（２Ｈ，ｄ），７．３６（２Ｈ，ｄ），３．２８−３．２０（２Ｈ，ｍ），２．８７−２．８０（２Ｈ，ｍ） Production Example 1-1: Production of compound represented by formula (1-1) <Production of compound represented by formula 9-1>

At room temperature, 10 g of the compound represented by the formula (10-1) and 15 ml of tetrahydrofuran were mixed and stirred, and the resulting mixture was cooled to 0 ° C. Then, 4.0 g of 95% acrolein and 0.1 g of triethylamine were added thereto. It was dripped. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 18.1 g of a compound represented by the formula (9-1).
1H NMR (CDCl ₃ )
δ ppm: 9.77 (1H, s), 7.51 (2H, d), 7.36 (2H, d), 3.28-3.20 (2H, m), 2.87-2.80 (2H, m)

室温にて、式（９−１）で示される化合物６５．７ｇおよびトリフェニルホスフィンアセチルメチレン１００ｇをクロロホルム３３０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−１）で示される化合物２８．６ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５２（２Ｈ，ｄ），７．３９（２Ｈ，ｄ），６．８２−６．７４（１Ｈ，ｍ），６．１３（１Ｈ，ｄｄ），３．１１（２Ｈ，ｍ），２．６３−２．５６（２Ｈ，ｍ），２．２３（３Ｈ，ｓ） <Production of Compound represented by Formula 7-1>

At room temperature, 65.7 g of the compound represented by the formula (9-1) and 100 g of triphenylphosphine acetylmethylene were dissolved in 330 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 28.6 g of a compound represented by the formula (7-1).
1H NMR (CDCl ₃ )
δ ppm: 7.52 (2H, d), 7.39 (2H, d), 6.82-6.74 (1H, m), 6.13 (1H, dd), 3.11 (2H, m ), 2.63-2.56 (2H, m), 2.23 (3H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液２２ｇおよび式（８−１）で示される化合物７．６ｇをテトラヒドロフラン２５０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−１）で示される化合物２８．６ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−１）で示される化合物２４．５ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：７．６３（２Ｈ，ｄ），７．４５（２Ｈ，ｄ），４．３９（１Ｈ，ｓ），３．４６（３Ｈ，ｓ），３．１１（１Ｈ，ｍ），２．９５（１Ｈ，ｍ），２．８３（１Ｈ，ｄ），２．３４−２．２６（１Ｈ，ｍ），２．１２（１Ｈ，ｄｄ），１．７８（１Ｈ，ｄｄ），１．５３−１．４７（２Ｈ，ｍ） <Production of Compound represented by Formula 6-1>

At room temperature, 22 g of 28% sodium methoxide methanol solution and 7.6 g of the compound represented by the formula (8-1) were dissolved in 250 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 28.6 g of the compound represented by the formula (7-1) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The obtained reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane in order to obtain 24.5 g of a compound represented by the formula (6-1).
1H NMR (d-DMSO)
δ ppm: 7.63 (2H, d), 7.45 (2H, d), 4.39 (1H, s), 3.46 (3H, s), 3.11 (1H, m), 2. 95 (1H, m), 2.83 (1H, d), 2.34-2.26 (1H, m), 2.12 (1H, dd), 1.78 (1H, dd), 1.53 -1.47 (2H, m)

室温にて、式（６−１）で示される化合物１２ｇを水１８０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム１０ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−１）で示される化合物１８ｇを得た。
１Ｈ ＮＭＲ （ｄ−ＤＭＳＯ）
δ ｐｐｍ：１１．０７（１Ｈ，ｓ），７．６３（２Ｈ，ｄ），７．４８（２Ｈ，ｄ），５．２２（１Ｈ，ｓ），３．１６−３．０５（２Ｈ，ｍ），２．３３−１．６９（７Ｈ，ｍ） <Production of compound represented by formula 2-1>

At room temperature, 12 g of the compound represented by formula (6-1) was dissolved in 180 ml of water. 10 g of anhydrous sodium carbonate was added to the resulting solution. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 18 g of a compound represented by the formula (2-1).
1H NMR (d-DMSO)
δ ppm: 11.07 (1H, s), 7.63 (2H, d), 7.48 (2H, d), 5.22 (1H, s), 3.16-3.05 (2H, m ), 2.33-1.69 (7H, m)

窒素雰囲気下、室温にて、四酢酸鉛２６．５ｇ、酢酸水銀０．８３ｇおよび式（５−１）で示される化合物１０ｇをクロロホルム１１０ｍｌに溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、反応液を４０℃で４時間攪拌した。反応液を室温まで冷却し、セライト（登録商標）濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質にヘキサンを加え、得られたものを減圧濃縮して黄色固体を得た。窒素雰囲気下、室温にて、得られた固体をクロロホルム２６０ｍｌに溶解した。得られた溶液に炭酸カリウム８６．２ｇを加え、得られたものを１０分間すばやく攪拌した。その後、反応液をセライト（登録商標）濾過した。得られたろ液を減圧濃縮し、式（３−１）で示される化合物２１ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．０５（２Ｈ，ｓ），２．９０（４Ｈ，ｍ），２．３５（３Ｈ，ｓ），２．０６（９Ｈ，ｓ），１．３３−１．２７（６Ｈ，ｍ） <Production of Compound represented by Formula 3-1>

Under a nitrogen atmosphere, at room temperature, 26.5 g of lead tetraacetate, 0.83 g of mercury acetate and 10 g of the compound represented by the formula (5-1) were dissolved in 110 ml of chloroform. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, the reaction solution was stirred at 40 ° C. for 4 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature and filtered through Celite (registered trademark). The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. Hexane was added to the obtained oily substance, and the obtained substance was concentrated under reduced pressure to obtain a yellow solid. The obtained solid was dissolved in 260 ml of chloroform at room temperature under a nitrogen atmosphere. To the obtained solution, 86.2 g of potassium carbonate was added, and the resultant was rapidly stirred for 10 minutes. Thereafter, the reaction solution was filtered through Celite (registered trademark). The obtained filtrate was concentrated under reduced pressure to obtain 21 g of a compound represented by the formula (3-1).
1H NMR (CDCl ₃ )
δ ppm: 7.05 (2H, s), 2.90 (4H, m), 2.35 (3H, s), 2.06 (9H, s), 1.33-1.27 (6H, m) )

窒素雰囲気下、室温にて、式（２−１）で示される化合物２４０ｍｇおよびジメチルアミノピリジン４６０ｍｇをクロロホルム２．５ｍｌとトルエン０．５ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物４４０ｍｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１−１）で示される化合物１２０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５４（２Ｈ，ｄ），７．３８（２Ｈ，ｄ），６．９８（２Ｈ，ｓ），５．５０（１Ｈ，ｓ），３．０７（２Ｈ，ｄｄｄ），２．７１（２Ｈ，ｔｄ），２．４７−２．２４（１０Ｈ，ｍ），１．８８（２Ｈ，ｑ），１．１０−１．０３（６Ｈ，ｍ） <Production of compound represented by formula 1-1>

Under a nitrogen atmosphere, at room temperature, 240 mg of the compound represented by formula (2-1) and 460 mg of dimethylaminopyridine were dissolved in a mixture of 2.5 ml of chloroform and 0.5 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 440 mg of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 120 mg of a compound represented by the formula (1-1).
1H NMR (CDCl ₃ )
δ ppm: 7.54 (2H, d), 7.38 (2H, d), 6.98 (2H, s), 5.50 (1H, s), 3.07 (2H, ddd), 2. 71 (2H, td), 2.47-2.24 (10H, m), 1.88 (2H, q), 1.10-1.03 (6H, m)

窒素雰囲気下、室温にて、四酢酸鉛６．２ｇ、酢酸水銀１９４ｍｇおよび式（５−２）で示される化合物２ｇをクロロホルム２５ｍｌに溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、反応液を４０℃で４時間攪拌した。反応液を室温まで冷却し、セライト（登録商標）濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質にヘキサンを加え、得られたものを減圧濃縮して黄色固体を得た。窒素雰囲気下、室温にて、得られた固体をクロロホルム５０ｍｌに溶解した。得られた溶液に炭酸カリウム２０ｇを加え、得られたものを１０分間すばやく攪拌した。その後、反応液をセライト（登録商標）濾過した。得られたろ液を減圧濃縮し、式（３−２）で示される化合物４ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：６．９９（２Ｈ，ｓ），２．５７（６Ｈ，ｓ），２．３０（３Ｈ，ｓ），２．０６（９Ｈ，ｓ） Production Example 1-2: Production of compound represented by formula (1-2) <Production of compound represented by formula 3-2>

Under a nitrogen atmosphere, at room temperature, 6.2 g of lead tetraacetate, 194 mg of mercury acetate and 2 g of the compound represented by the formula (5-2) were dissolved in 25 ml of chloroform. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, the reaction solution was stirred at 40 ° C. for 4 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature and filtered through Celite (registered trademark). The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. Hexane was added to the obtained oily substance, and the obtained substance was concentrated under reduced pressure to obtain a yellow solid. The obtained solid was dissolved in 50 ml of chloroform at room temperature under a nitrogen atmosphere. 20 g of potassium carbonate was added to the resulting solution, and the resulting solution was rapidly stirred for 10 minutes. Thereafter, the reaction solution was filtered through Celite (registered trademark). The obtained filtrate was concentrated under reduced pressure to obtain 4 g of a compound represented by the formula (3-2).
1H NMR (CDCl ₃ )
δ ppm: 6.99 (2H, s), 2.57 (6H, s), 2.30 (3H, s), 2.06 (9H, s)

窒素雰囲気下、室温にて、式（２−１）で示される化合物２４０ｍｇおよびジメチルアミノピリジン４６０ｍｇをクロロホルム２．５ｍｌとトルエン０．５ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−２）で示される化合物４２０ｍｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１−２）で示される化合物１２５ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５４（２Ｈ，ｄ），７．３７（２Ｈ，ｄ），６．９４（２Ｈ，ｓ），５．７２（１Ｈ，ｓ），３．１１−３．０１（２Ｈ，ｍ），２．７０（２Ｈ，ｔｄ），２．４４−２．０１（１２Ｈ，ｍ），１．８７（２Ｈ，ｑ） <Production of compound represented by formula 1-2>

Under a nitrogen atmosphere, at room temperature, 240 mg of the compound represented by formula (2-1) and 460 mg of dimethylaminopyridine were dissolved in a mixture of 2.5 ml of chloroform and 0.5 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 420 mg of the compound represented by the formula (3-2) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 125 mg of the compound represented by the formula (1-2).
1H NMR (CDCl ₃ )
δ ppm: 7.54 (2H, d), 7.37 (2H, d), 6.94 (2H, s), 5.72 (1H, s), 3.11-3.01 (2H, m ), 2.70 (2H, td), 2.44-2.01 (12H, m), 1.87 (2H, q)

窒素雰囲気下、室温にて、四酢酸鉛８．４ｇ、酢酸水銀２６３ｍｇおよび式（５−３）で示される化合物４．２ｇをクロロホルム３５ｍｌに溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、反応液を４０℃で４時間攪拌した。反応液を室温まで冷却し、セライト（登録商標）濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質にヘキサンを加え、得られたものを減圧濃縮して黄色固体を得た。窒素雰囲気下、室温にて、得られた固体をクロロホルム８０ｍｌに溶解した。得られた溶液に炭酸カリウム２７．４ｇを加え、得られたものを１０分間すばやく攪拌した。その後、反応液をセライト（登録商標）濾過した。得られたろ液を減圧濃縮し、式（３−３）で示される化合物６．４ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．６０−７．３１（７Ｈ，ｍ），３．０６−２．９３（４Ｈ，ｍ），２．０７（９Ｈ，ｓ），１．３９−１．３２（６Ｈ，ｍ） Production Example 1-3: Production of compound represented by formula (1-3) <Production of compound represented by formula 3-3>

Under a nitrogen atmosphere, at room temperature, 8.4 g of lead tetraacetate, 263 mg of mercury acetate and 4.2 g of the compound represented by the formula (5-3) were dissolved in 35 ml of chloroform. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, the reaction solution was stirred at 40 ° C. for 4 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature and filtered through Celite (registered trademark). The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. Hexane was added to the obtained oily substance, and the obtained substance was concentrated under reduced pressure to obtain a yellow solid. The obtained solid was dissolved in 80 ml of chloroform at room temperature under a nitrogen atmosphere. To the obtained solution was added 27.4 g of potassium carbonate, and the resulting product was rapidly stirred for 10 minutes. Thereafter, the reaction solution was filtered through Celite (registered trademark). The obtained filtrate was concentrated under reduced pressure to obtain 6.4 g of a compound represented by the formula (3-3).
1H NMR (CDCl ₃ )
δ ppm: 7.60-7.31 (7H, m), 3.06-2.93 (4H, m), 2.07 (9H, s), 1.39-1.32 (6H, m)

窒素雰囲気下、室温にて、式（２−１）で示される化合物２４０ｍｇおよびジメチルアミノピリジン４６０ｍｇをクロロホルム２．５ｍｌとトルエン０．５ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−３）で示される化合物５００ｍｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１−３）で示される化合物１９０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５７（４Ｈ，ｔｄ），７．４５（２Ｈ，ｄｄ），７．４０−７．３４（５Ｈ，ｍ），５．５６（１Ｈ，ｓ），３．１０（２Ｈ，ｄｔ），２．７８−２．７１（２Ｈ，ｍ），２．５３−２．３０（７Ｈ，ｍ），１．９０（２Ｈ，ｑ），１．１７−１．０９（６Ｈ，ｍ） <Production of compound represented by formula 1-3>

Under a nitrogen atmosphere, at room temperature, 240 mg of the compound represented by formula (2-1) and 460 mg of dimethylaminopyridine were dissolved in a mixture of 2.5 ml of chloroform and 0.5 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 500 mg of the compound represented by the formula (3-3) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 190 mg of a compound represented by the formula (1-3).
1H NMR (CDCl ₃ )
δ ppm: 7.57 (4H, td), 7.45 (2H, dd), 7.40-7.34 (5H, m), 5.56 (1H, s), 3.10 (2H, dt) ), 2.78-2.71 (2H, m), 2.53-2.30 (7H, m), 1.90 (2H, q), 1.17-1.09 (6H, m)

室温にて、式（１０−２）で示される化合物１０ｇおよびテトラヒドロフラン３０ｍｌを混合、を攪拌し、得られた混合物を０℃まで冷却した後、そこに９５％アクロレイン４．０ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水洗し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−２）で示される化合物１３ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．８０（１Ｈ，ｓ），８，６７−８．６６（１Ｈ，ｍ），７．６７（１Ｈ，ｄｄ），７．２６(１Ｈ，ｄｄ)，３．４８（２Ｈ，ｄｄｄ），２．９８−２．９５（２Ｈ，ｍ） Production Example 1-4: Production of compound represented by formula (1-4) <Production of compound represented by formula 9-2>

The mixture was stirred at room temperature with 10 g of the compound represented by formula (10-2) and 30 ml of tetrahydrofuran, and the resulting mixture was cooled to 0 ° C., and then 4.0 g of 95% acrolein and 0.1 g of triethylamine Was dripped. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 13 g of a compound represented by the formula (9-2).
1H NMR (CDCl ₃ )
δ ppm: 9.80 (1H, s), 8, 67-8.66 (1H, m), 7.67 (1H, dd), 7.26 (1H, dd), 3.48 (2H, ddd) ), 2.98-2.95 (2H, m)

室温にて、式（９−２）で示される化合物１３ｇおよびトリフェニルホスフィンアセチルメチレン２０ｇをクロロホルム６５ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−２）で示される化合物１３ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６７（１Ｈ，ｄｄ），７．６９−７．６６（１Ｈ，ｍ），７．２９（１Ｈ，ｄ），６．８８−６．８０（１Ｈ，ｍ），６．１６（１Ｈ，ｄｔ），３．３６（２Ｈ，ｔ），２．６７（２Ｈ，ｔｔ），２．２４（３Ｈ，ｓ） <Production of Compound represented by Formula 7-2>

At room temperature, 13 g of the compound represented by the formula (9-2) and 20 g of triphenylphosphine acetylmethylene were dissolved in 65 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 13 g of a compound represented by the formula (7-2).
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, dd), 7.69-7.66 (1H, m), 7.29 (1H, d), 6.88-6.80 (1H, m), 6.16 (1H, dt), 3.36 (2H, t), 2.67 (2H, tt), 2.24 (3H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液１０ｇおよび式（８−１）で示される化合物６．７ｇをテトラヒドロフラン１３０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−２）で示される化合物１３ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−２）で示される化合物１５．４ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：８．７８（１Ｈ，ｄ），７．９８（１Ｈ，ｄｄ），７．５０（１Ｈ，ｄ），４．４０（１Ｈ，ｓ），３．４９（３Ｈ，ｓ），３．２６（１Ｈ，ｄｑ），３．０６（１Ｈ，ｄｔ），２．８３（１Ｈ，ｄ），２．３４−２．２４（１Ｈ，ｍ），２．１３（１Ｈ，ｄｄ），１．７９（１Ｈ，ｄｔ），１．６３−１．４９（２Ｈ，ｍ） <Production of Compound represented by Formula 6-2>

At room temperature, 10 g of 28% sodium methoxide methanol solution and 6.7 g of the compound represented by the formula (8-1) were dissolved in 130 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 13 g of the compound represented by the formula (7-2) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The obtained reaction liquid was cooled to room temperature, and the precipitated crystals were collected by filtration and washed well with tert-butyl methyl ether and hexane in order to obtain 15.4 g of a compound represented by the formula (6-2).
1H NMR (d-DMSO)
δ ppm: 8.78 (1H, d), 7.98 (1H, dd), 7.50 (1H, d), 4.40 (1H, s), 3.49 (3H, s), 3. 26 (1H, dq), 3.06 (1H, dt), 2.83 (1H, d), 2.34-2.24 (1H, m), 2.13 (1H, dd), 1.79 (1H, dt), 1.63-1.49 (2H, m)

室温にて、式（６−２）で示される化合物５ｇを水７０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム４ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶を順次、ｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで洗浄して式（２−２）で示される化合物３．１ｇを得た。
１Ｈ ＮＭＲ （ｄ−ＤＭＳＯ）
δ ｐｐｍ：１１．０７（１Ｈ，ｓ），８．８０（１Ｈ，ｄ），７．９８（１Ｈ，ｄｄ），７．５２(１Ｈ，ｄ)，５．２１（１Ｈ，ｓ），３．２３（２Ｈ，ｔ），２．３４（２Ｈ，ｄ），２．１３（３Ｈ，ｍ），１．７３（２Ｈ，ｍ） <Production of compound represented by formula 2-2>

At room temperature, 5 g of the compound represented by the formula (6-2) was dissolved in 70 ml of water. To the resulting solution was added 4 g of anhydrous sodium carbonate. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 3.1 g of a compound represented by the formula (2-2).
1H NMR (d-DMSO)
δ ppm: 11.07 (1H, s), 8.80 (1H, d), 7.98 (1H, dd), 7.52 (1H, d), 5.21 (1H, s), 3. 23 (2H, t), 2.34 (2H, d), 2.13 (3H, m), 1.73 (2H, m)

窒素雰囲気下、室温にて、式（２−２）で示される化合物５４０ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１−４）で示される化合物３２０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６８−８．６７（１Ｈ，ｍ），７．６７（１Ｈ，ｄｄ），７．２７（１Ｈ，ｄ），６．９８(２Ｈ，ｓ)，５．５２（１Ｈ，ｓ），３．３１（２Ｈ，ｔｔ），２．７５（２Ｈ，ｄｄｄ），２．５１−２．２３（１０Ｈ，ｍ），１．９２（２Ｈ，ｄｄｄ），１．５（６Ｈ，ｄｔ） <Production of compound represented by formula 1-4>

Under a nitrogen atmosphere, at room temperature, 540 mg of the compound represented by the formula (2-2) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 320 mg of the compound represented by the formula (1-4).
1H NMR (CDCl ₃ )
δ ppm: 8.68-8.67 (1H, m), 7.67 (1H, dd), 7.27 (1H, d), 6.98 (2H, s), 5.52 (1H, s ), 3.31 (2H, tt), 2.75 (2H, ddd), 2.51-2.23 (10H, m), 1.92 (2H, ddd), 1.5 (6H, dt)

窒素雰囲気下、室温にて、式（２−２）で示される化合物５７０ｍｇおよびジメチルアミノピリジン１．１ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−２）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１−５）で示される化合物４１０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６６（１Ｈ，ｓ），７．６６（１Ｈ，ｄｄ），７．２６(１Ｈ，ｄ)，６．９３（２Ｈ，ｓ），５．６６（１Ｈ，ｓ），３．３２−３．２８（２Ｈ，ｍ），２．７４（２Ｈ，ｔ），２．４６−２．０４（１２Ｈ，ｍ），１．９１（２Ｈ，ｍ） Production Example 1-5: Production of compound represented by formula (1-5) <Production of compound represented by formula 1-5>

Under a nitrogen atmosphere, at room temperature, 570 mg of the compound represented by formula (2-2) and 1.1 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-2) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 410 mg of the compound represented by the formula (1-5).
1H NMR (CDCl ₃ )
δ ppm: 8.66 (1H, s), 7.66 (1H, dd), 7.26 (1H, d), 6.93 (2H, s), 5.66 (1H, s), 3. 32-3.28 (2H, m), 2.74 (2H, t), 2.46-2.04 (12H, m), 1.91 (2H, m)

室温にて、式（１０−３）で示される化合物１０ｇおよびテトラヒドロフラン３０ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこに９５％アクロレイン６．６ｇとトリエチルアミン０．２ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水洗し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−３）で示される化合物１５ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．７４（１Ｈ，ｓ），７．３６−７．１７（５Ｈ，ｍ），３．１７（２Ｈ，ｔ），２．７５（２Ｈ，ｔ） Production Example 1-6: Production of compound represented by formula (1-6) <Production of compound represented by formula 9-3>

At room temperature, 10 g of the compound represented by the formula (10-3) and 30 ml of tetrahydrofuran were mixed and stirred, and the resulting mixture was cooled to 0 ° C. Then, 6.6 g of 95% acrolein and 0.2 g of triethylamine were added thereto. It was dripped. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 15 g of a compound represented by the formula (9-3).
1H NMR (CDCl ₃ )
δ ppm: 9.74 (1H, s), 7.36-7.17 (5H, m), 3.17 (2H, t), 2.75 (2H, t)

室温にて、式（９−３）で示される化合物１０ｇおよびトリフェニルホスフィンアセチルメチレン２１ｇをクロロホルム７０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−３）で示される化合物７．２ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３５−７．２５（４Ｈ，ｍ），７．１８（１Ｈ，ｍ），６．８０−６．７１（１Ｈ，ｍ），６．０７（１Ｈ，ｄｔ），３．０１（２Ｈ，ｔｔ），２．５１（２Ｈ，ｄｄｄ），２．２３（３Ｈ，ｓ） <Production of compound represented by formula 7-3>

At room temperature, 10 g of the compound represented by the formula (9-3) and 21 g of triphenylphosphine acetylmethylene were dissolved in 70 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 7.2 g of a compound represented by the formula (7-3).
1H NMR (CDCl ₃ )
δ ppm: 7.35-7.25 (4H, m), 7.18 (1H, m), 6.80-6.71 (1H, m), 6.07 (1H, dt), 3.01 (2H, tt), 2.51 (2H, ddd), 2.23 (3H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液７．５ｇおよび式（８−１）で示される化合物５ｇをテトラヒドロフラン１００ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−３）で示される化合物７．２ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−３）で示される化合物１０ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：７．３３−７．２７（４Ｈ，ｍ），７．１７（１Ｈ，ｄｑ），４．３７（１Ｈ，ｓ），３．４８（３Ｈ，ｓ），３．０２−２．９６（１Ｈ，ｍ），２．８７−２．７８（２Ｈ，ｍ），２．３３−２．２３（１Ｈ，ｍ），２．０８（１Ｈ，ｄｄ），１．７４（１Ｈ，ｄｄ），１．４４（２Ｈ，ｍ） <Production of compound represented by formula 6-3>

At room temperature, 7.5 g of 28% sodium methoxide methanol solution and 5 g of the compound represented by the formula (8-1) were dissolved in 100 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 7.2 g of the compound represented by the formula (7-3) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The obtained reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane to obtain 10 g of a compound represented by the formula (6-3).
1H NMR (d-DMSO)
δ ppm: 7.33-7.27 (4H, m), 7.17 (1H, dq), 4.37 (1H, s), 3.48 (3H, s), 3.02-2.96 (1H, m), 2.87-2.78 (2H, m), 2.3-2.23 (1H, m), 2.08 (1H, dd), 1.74 (1H, dd), 1.44 (2H, m)

室温にて、式（６−３）で示される化合物５ｇを水８０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム４．８ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−３）で示される化合物３．４ｇを得た。
１Ｈ ＮＭＲ （ｄ−ＤＭＳＯ）
δ ｐｐｍ：１１．０５（１Ｈ，ｓ），７．３１（４Ｈ，ｍ），７．１８（１Ｈ，ｍ），５．１９（１Ｈ，ｓ），３．００（２Ｈ，ｔ），２．３３−１．９９（５Ｈ，ｍ），１．６３（２Ｈ，ｍ） <Production of compound represented by formula 2-3>

At room temperature, 5 g of the compound represented by the formula (6-3) was dissolved in 80 ml of water. To the resulting solution was added anhydrous sodium carbonate 4.8 g. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 3.4 g of a compound represented by the formula (2-3).
1H NMR (d-DMSO)
δ ppm: 11.05 (1H, s), 7.31 (4H, m), 7.18 (1H, m), 5.19 (1H, s), 3.00 (2H, t), 2. 33-1.99 (5H, m), 1.63 (2H, m)

窒素雰囲気下、室温にて、式（２−３）で示される化合物４３０ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−６）で示される化合物３１０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３６−７．２０（５Ｈ，ｍ），６．９７（２Ｈ，ｓ），５．５９（１Ｈ，ｓ），３．００（２Ｈ，ｄｄｄ），２．６７（２Ｈ，ｄｄｔ），２．４７−２．２０（１０Ｈ，ｍ），１．８２（２Ｈ，ｑ），１．１０−１．０２（６Ｈ，ｍ） <Production of compound represented by formula 1-6>

Under a nitrogen atmosphere, at room temperature, 430 mg of the compound represented by the formula (2-3) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 310 mg of the compound represented by the formula (1-6).
1H NMR (CDCl ₃ )
δ ppm: 7.36-7.20 (5H, m), 6.97 (2H, s), 5.59 (1H, s), 3.00 (2H, ddd), 2.67 (2H, ddt) ), 2.47-2.20 (10H, m), 1.82 (2H, q), 1.10-1.02 (6H, m)

室温にて、式（１０−４）で示される化合物５ｇおよびテトラヒドロフラン１５ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこに９５％アクロレイン３．０ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水洗し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−４）で示される化合物７．４ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．７２（１Ｈ，ｓ），７．２４（２Ｈ，ｄ），７．１８（２Ｈ，ｄ），３．１２（２Ｈ，ｔ），２．７１（２Ｈ，ｔ），２．３１（３Ｈ，ｓ） Production Example 1-7: Production of compound represented by formula (1-7) <Production of compound represented by formula 9-4>

At room temperature, 5 g of the compound represented by the formula (10-4) and 15 ml of tetrahydrofuran were mixed and stirred, and the resulting mixture was cooled to 0 ° C. Then, 3.0 g of 95% acrolein and 0.1 g of triethylamine were added thereto. It was dripped. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 7.4 g of a compound represented by the formula (9-4).
1H NMR (CDCl ₃ )
δ ppm: 9.72 (1H, s), 7.24 (2H, d), 7.18 (2H, d), 3.12 (2H, t), 2.71 (2H, t), 2. 31 (3H, s)

室温にて、式（９−４）で示される化合物７．４ｇおよびトリフェニルホスフィンアセチルメチレン１４．４ｇをクロロホルム５０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−４）で示される化合物６．０ｇを得た。
引き続き、室温にて、２８％ナトリウムメトキシドメタノール溶液５．８ｇおよび式（８−１）で示される化合物４．０ｇをテトラヒドロフラン８０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−４）で示される化合物６．０ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−４）で示される化合物６．７ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：７．１９（２Ｈ，ｄ），７．１２（２Ｈ，ｄ），４．３９（１Ｈ，ｓ），３．４８（３Ｈ，ｓ），２．９７−２．９０（１Ｈ，ｍ），２．８２−２．７５（２Ｈ，ｍ），２．２４（３Ｈ，ｓ），２．１０−２．０４（１Ｈ，ｍ），１．７２（１Ｈ，ｄｄ），１．４９−１．３５（２Ｈ，ｍ） <Production of compound represented by formula 6-4>

At room temperature, 7.4 g of the compound represented by the formula (9-4) and 14.4 g of triphenylphosphine acetylmethylene were dissolved in 50 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 6.0 g of a compound represented by the formula (7-4).
Subsequently, 5.8 g of 28% sodium methoxide methanol solution and 4.0 g of the compound represented by the formula (8-1) were dissolved in 80 ml of tetrahydrofuran at room temperature. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 6.0 g of the compound represented by the formula (7-4) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The obtained reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane in order to obtain 6.7 g of a compound represented by the formula (6-4).
1H NMR (d-DMSO)
δ ppm: 7.19 (2H, d), 7.12 (2H, d), 4.39 (1H, s), 3.48 (3H, s), 2.97-2.90 (1H, m ), 2.82-2.75 (2H, m), 2.24 (3H, s), 2.10-2.04 (1H, m), 1.72 (1H, dd), 1.49- 1.35 (2H, m)

室温にて、式（６−４）で示される化合物５ｇを水８０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム４．６ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンとで順次洗浄して式（２−４）で示される化合物２．９ｇを得た。
１Ｈ ＮＭＲ （ｄ−ＤＭＳＯ）
δ ｐｐｍ：１１．０４（１Ｈ，ｓ），７．２３（２Ｈ，ｄ），７．１３（２Ｈ，ｄ），５．１９（１Ｈ，ｓ），２．９５（２Ｈ，ｔ），２．４２−１．９９（８Ｈ，ｍ），１．６０−１．５８（２Ｈ，ｍ） <Production of compound represented by formula 2-4>

At room temperature, 5 g of the compound represented by the formula (6-4) was dissolved in 80 ml of water. 4.6 g of anhydrous sodium carbonate was added to the resulting solution. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 2.9 g of a compound represented by the formula (2-4).
1H NMR (d-DMSO)
δ ppm: 11.04 (1H, s), 7.23 (2H, d), 7.13 (2H, d), 5.19 (1H, s), 2.95 (2H, t), 2. 42-1.99 (8H, m), 1.60-1.58 (2H, m)

窒素雰囲気下、室温にて、式（２−４）で示される化合物４５０ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−７）で示される化合物３４０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．２７（２Ｈ，ｄ），７．１２（２Ｈ，ｄ），６．９８（２Ｈ，ｓ），５．４７（１Ｈ，ｓ），２．９６（２Ｈ，ｄｔ），２．６７（２Ｈ，ｄｄｄ），２．４５−２．２１（１３Ｈ，ｍ），１．８０（２Ｈ，ｑ），１．０６（６Ｈ，ｄｔ） <Production of compound represented by formula 1-7>

Under a nitrogen atmosphere, at room temperature, 450 mg of the compound represented by formula (2-4) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 340 mg of a compound represented by the formula (1-7).
1H NMR (CDCl ₃ )
δ ppm: 7.27 (2H, d), 7.12 (2H, d), 6.98 (2H, s), 5.47 (1H, s), 2.96 (2H, dt), 2. 67 (2H, ddd), 2.45-2.21 (13H, m), 1.80 (2H, q), 1.06 (6H, dt)

室温にて、式（１０−５）で示される化合物４ｇおよびテトラヒドロフラン１５ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこに９５％アクロレイン２．５ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水洗し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−５）で示される化合物５．５ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．７３（１Ｈ，ｓ），７．３６（２Ｈ，ｄ），６．８５（２Ｈ，ｄ），３．８０（３Ｈ，ｓ），３．０６(２Ｈ，ｔ)，２．６８（２Ｈ，ｔ） Production Example 1-8: Production of compound represented by formula (1-8) <Production of compound represented by formula 9-5>

At room temperature, 4 g of the compound represented by the formula (10-5) and 15 ml of tetrahydrofuran were mixed and stirred, and the resulting mixture was cooled to 0 ° C. Then, 2.5 g of 95% acrolein and 0.1 g of triethylamine were added thereto. It was dripped. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 5.5 g of a compound represented by the formula (9-5).
1H NMR (CDCl ₃ )
δ ppm: 9.73 (1H, s), 7.36 (2H, d), 6.85 (2H, d), 3.80 (3H, s), 3.06 (2H, t), 2. 68 (2H, t)

室温にて、式（９−５）で示される化合物５．５ｇおよびトリフェニルホスフィンアセチルメチレン１０ｇをクロロホルム４０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−５）で示される化合物５．４ｇを得た。
引き続き、室温にて、２８％ナトリウムメトキシドメタノール溶液４．８ｇおよび式（８−１）で示される化合物３．３ｇをテトラヒドロフラン７０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−５）で示される化合物５．４ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−５）で示される化合物５．７ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：７．２８（２Ｈ，ｄ），６．９０（２Ｈ，ｄ），４．３８（１Ｈ，ｓ），３．７５（３Ｈ，ｓ），３．４７（３Ｈ，ｓ），２．９０−２．６９（３Ｈ，ｍ），２．３０−２．２２（１Ｈ，ｍ），２．０４（１Ｈ，ｄｄ），１．７４−１．６６（１Ｈ，ｍ），１．４５−１．３３（２Ｈ，ｍ） <Production of compound represented by formula 6-5>

At room temperature, 5.5 g of the compound represented by the formula (9-5) and 10 g of triphenylphosphine acetylmethylene were dissolved in 40 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 5.4 g of a compound represented by the formula (7-5).
Subsequently, at room temperature, 4.8 g of 28% sodium methoxide methanol solution and 3.3 g of the compound represented by the formula (8-1) were dissolved in 70 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 5.4 g of the compound represented by the formula (7-5) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The resulting reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane to obtain 5.7 g of a compound represented by the formula (6-5).
1H NMR (d-DMSO)
δ ppm: 7.28 (2H, d), 6.90 (2H, d), 4.38 (1H, s), 3.75 (3H, s), 3.47 (3H, s), 2. 90-2.69 (3H, m), 2.30-2.22 (1H, m), 2.04 (1H, dd), 1.74-1.66 (1H, m), 1.45 1.33 (2H, m)

室温にて、式（６−５）で示される化合物５ｇを水８０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム４．４ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−５）で示される化合物３．８ｇを得た。
引き続き、窒素雰囲気下、室温にて、式（２−５）で示される化合物４８０ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１−８）で示される化合物１７４ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３６（２Ｈ，ｄｄ），６．９７（２Ｈ，ｄ），６．８６（２Ｈ，ｄｄ），５．５７（１Ｈ，ｓ），３．８０(３Ｈ，３Ｈ)，２．９２−２．８８（２Ｈ，ｍ），２．６９―２．６０（２Ｈ，ｍ），２．４４−２．１９（１０Ｈ，ｍ），１．７５（２Ｈ，ｄｄ），１．０６（６Ｈ，ｄｔ） <Production of compound represented by formula 1-8>

At room temperature, 5 g of the compound represented by the formula (6-5) was dissolved in 80 ml of water. 4.4 g of anhydrous sodium carbonate was added to the resulting solution. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 3.8 g of a compound represented by the formula (2-5).
Subsequently, 480 mg of the compound represented by the formula (2-5) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene at room temperature under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 174 mg of a compound represented by the formula (1-8).
1H NMR (CDCl ₃ )
δ ppm: 7.36 (2H, dd), 6.97 (2H, d), 6.86 (2H, dd), 5.57 (1H, s), 3.80 (3H, 3H), 2. 92-2.88 (2H, m), 2.69-2.60 (2H, m), 2.44-2.19 (10H, m), 1.75 (2H, dd), 1.06 ( 6H, dt)

室温にて、式（１０−６）で示される化合物１０ｇおよびテトラヒドロフラン２０ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこに９５％アクロレイン５．６ｇとトリエチルアミン０．２ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水洗し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−６）で示される化合物１３ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．７３（１Ｈ，ｓ），７．２９―７．２０（４Ｈ，ｍ），３．１４（２Ｈ，ｔ），２．７５（２Ｈ，ｔ） Production Example 1-9: Production of compound represented by formula (1-9) <Production of compound represented by formula 9-6>

At room temperature, 10 g of the compound represented by the formula (10-6) and 20 ml of tetrahydrofuran were mixed and stirred, and the resulting mixture was cooled to 0 ° C. Then, 5.6 g of 95% acrolein and 0.2 g of triethylamine were added thereto. It was dripped. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 13 g of a compound represented by the formula (9-6).
1H NMR (CDCl ₃ )
δ ppm: 9.73 (1H, s), 7.29-7.20 (4H, m), 3.14 (2H, t), 2.75 (2H, t)

室温にて、式（９−６）で示される化合物１０ｇおよびトリフェニルホスフィンアセチルメチレン１７．４ｇをクロロホルム６０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−６）で示される化合物９．４ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３１−７．２２（４Ｈ，ｍ），６．８０−６．７０（１Ｈ，ｍ），６．０８（１Ｈ，ｄ），３．００（２Ｈ，ｍ），２．５２（２Ｈ，ｍ），２．２３（３Ｈ，ｓ） <Production of Compound represented by Formula 7-6>

At room temperature, 10 g of the compound represented by the formula (9-6) and 17.4 g of triphenylphosphine acetylmethylene were dissolved in 60 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 9.4 g of a compound represented by the formula (7-6).
1H NMR (CDCl ₃ )
δ ppm: 7.31-7.22 (4H, m), 6.80-6.70 (1H, m), 6.08 (1H, d), 3.00 (2H, m), 2.52 (2H, m), 2.23 (3H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液８．３ｇおよび式（８−１）で示される化合物５．７ｇをテトラヒドロフラン１００ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−６）で示される化合物９．４ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−６）で示される化合物１０ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：７．３６（２Ｈ，ｄ），７．３０（２Ｈ，ｄ），４．３８（１Ｈ，ｓ），３．４８（３Ｈ，ｓ），３．００（１Ｈ，ｍ），２．８４（２Ｈ，ｍ），２．３２−２．２２（１Ｈ，ｍ），２．０９（１Ｈ，ｍ），１．７８―１．７１（１Ｈ，ｍ），１．４４（２Ｈ，ｍ） <Production of compound represented by formula 6-6>

At room temperature, 8.3 g of 28% sodium methoxide methanol solution and 5.7 g of the compound represented by the formula (8-1) were dissolved in 100 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 9.4 g of the compound represented by the formula (7-6) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The obtained reaction liquid was cooled to room temperature, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane to obtain 10 g of a compound represented by the formula (6-6).
1H NMR (d-DMSO)
δ ppm: 7.36 (2H, d), 7.30 (2H, d), 4.38 (1H, s), 3.48 (3H, s), 3.00 (1H, m), 2. 84 (2H, m), 2.32-2.22 (1H, m), 2.09 (1H, m), 1.78-1.71 (1H, m), 1.44 (2H, m)

室温にて、式（６−６）で示される化合物５ｇを水８０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム４．４ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−６）で示される化合物２．９ｇを得た。
１Ｈ ＮＭＲ （ｄ−ＤＭＳＯ）
δ ｐｐｍ：１１．０６（１Ｈ，ｓ），７．３６（４Ｈ，ｍ），５．１９（１Ｈ，ｓ），３．０１（２Ｈ，ｔ），２．３２−１．９９（５Ｈ，ｍ），１．６２（２Ｈ，ｍ） <Production of compound represented by formula 2-6>

At room temperature, 5 g of the compound represented by the formula (6-6) was dissolved in 80 ml of water. 4.4 g of anhydrous sodium carbonate was added to the resulting solution. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 2.9 g of the compound represented by the formula (2-6).
1H NMR (d-DMSO)
δ ppm: 11.06 (1H, s), 7.36 (4H, m), 5.19 (1H, s), 3.01 (2H, t), 2.32-1.99 (5H, m ), 1.62 (2H, m)

窒素雰囲気下、室温にて、式（２−６）で示される化合物４９０ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−９）で示される化合物３５０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．２９−７．２４（４Ｈ，ｍ），６．９７（２Ｈ，ｓ），５．６６（１Ｈ，ｓ），３．０２−２．９３（２Ｈ，ｍ），２．６６（２Ｈ，ｔｔ），２．４５−２．２１（１０Ｈ，ｍ），１．８０（２Ｈ，ｑ），１．１０−１．０１（６Ｈ，ｍ） <Production of Compound represented by Formula 1-9>

Under a nitrogen atmosphere, at room temperature, 490 mg of the compound represented by the formula (2-6) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 350 mg of the compound represented by the formula (1-9).
1H NMR (CDCl ₃ )
δ ppm: 7.29-7.24 (4H, m), 6.97 (2H, s), 5.66 (1H, s), 3.02-2.93 (2H, m), 2.66 (2H, tt), 2.45-2.21 (10H, m), 1.80 (2H, q), 1.10-1.01 (6H, m)

室温にて、式（１０−７）で示される化合物１０ｇおよびテトラヒドロフラン２５ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこに９５％アクロレイン６．７ｇとトリエチルアミン０．２ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水洗し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−７）で示される化合物１４ｇを得た。
引き続き、室温にて、式（９−７）で示される化合物１４ｇおよびトリフェニルホスフィンアセチルメチレン３０ｇをクロロホルム１００ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−７）で示される化合物１３ｇを得た。
引き続き、室温にて、２８％ナトリウムメトキシドメタノール溶液１２ｇおよび式（８−１）で示される化合物８．４ｇをテトラヒドロフラン１５０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−７）で示される化合物１３ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−７）で示される化合物１４．２ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：７．３６（２Ｈ，ｄｄｄ），７．１７（２Ｈ，ｔｔ），４．３７（１Ｈ，ｓ），３．４９（３Ｈ，ｓ），３．００−２．９３（１Ｈ，ｍ），２．８５―２．７７（２Ｈ，ｍ），２．２７（１Ｈ，ｔｄｄ），２．０６（１Ｈ，ｄｄ），１．７３（１Ｈ，ｄｔ），１．４２（２Ｈ，ｔｔ） Production Example 1-10: Production of compound represented by formula (1-10) <Production of compound represented by formula 6-7>

At room temperature, 10 g of the compound represented by the formula (10-7) and 25 ml of tetrahydrofuran were mixed and stirred, and the resulting mixture was cooled to 0 ° C. Then, 6.7 g of 95% acrolein and 0.2 g of triethylamine were added thereto. It was dripped. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 14 g of a compound represented by the formula (9-7).
Subsequently, at room temperature, 14 g of the compound represented by the formula (9-7) and 30 g of triphenylphosphine acetylmethylene were dissolved in 100 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 13 g of a compound represented by the formula (7-7).
Subsequently, 12 g of 28% sodium methoxide methanol solution and 8.4 g of the compound represented by the formula (8-1) were dissolved in 150 ml of tetrahydrofuran at room temperature. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 13 g of the compound represented by the formula (7-7) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The obtained reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane in order to obtain 14.2 g of a compound represented by the formula (6-7).
1H NMR (d-DMSO)
δ ppm: 7.36 (2H, ddd), 7.17 (2H, tt), 4.37 (1H, s), 3.49 (3H, s), 3.00-2.93 (1H, m ), 2.85-2.77 (2H, m), 2.27 (1H, tdd), 2.06 (1H, dd), 1.73 (1H, dt), 1.42 (2H, tt)

室温にて、式（６−７）で示される化合物５ｇを水８０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム４．６ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−７）で示される化合物２．４ｇを得た。
１Ｈ ＮＭＲ （ｄ−ＤＭＳＯ）
δ ｐｐｍ：１１．０４（１Ｈ，ｓ），７．４０（２Ｈ，ｄｄｄ），７．１７（２Ｈ，ｔｔ），５．１９（１Ｈ，ｓ），２．９８（２Ｈ，ｔ），２．２８−１．９１（５Ｈ，ｍ），１．６０（２Ｈ，ｄｄ） <Production of compound represented by formula 2-7>

At room temperature, 5 g of the compound represented by the formula (6-7) was dissolved in 80 ml of water. 4.6 g of anhydrous sodium carbonate was added to the resulting solution. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 2.4 g of a compound represented by the formula (2-7).
1H NMR (d-DMSO)
δ ppm: 11.04 (1H, s), 7.40 (2H, ddd), 7.17 (2H, tt), 5.19 (1H, s), 2.98 (2H, t), 2. 28-1.91 (5H, m), 1.60 (2H, dd)

窒素雰囲気下、室温にて、式（２−７）で示される化合物４６０ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−１０）で示される化合物３３０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３９−７．３３（２Ｈ，ｍ），７．０４−６．９８（２Ｈ，ｍ），６．９７（２Ｈ，ｓ），５．６２（１Ｈ，ｓ），２．９５（２Ｈ，ｄｄｄ），２．６５（２Ｈ，ｄｄ），２．４５−２．２１（１０Ｈ，ｍ），１．７８（２Ｈ，ｑ），１．０６（６Ｈ，ｄｄｄ） <Production of compound represented by formula 1-10>

Under a nitrogen atmosphere, at room temperature, 460 mg of the compound represented by the formula (2-7) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 330 mg of the compound represented by the formula (1-10).
1H NMR (CDCl ₃ )
δ ppm: 7.39-7.33 (2H, m), 7.04-6.98 (2H, m), 6.97 (2H, s), 5.62 (1H, s), 2.95 (2H, ddd), 2.65 (2H, dd), 2.45-2.21 (10H, m), 1.78 (2H, q), 1.06 (6H, ddd)

室温にて、式（１０−１）で示される化合物５ｇおよびテトラヒドロフラン１５ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこにメタクロレイン２．６ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水洗し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−８）で示される化合物６．９ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．６９（１Ｈ，ｓ），７．５３（２Ｈ，ｄ），７．４０（２Ｈ，ｄ），３．４２−３．３５（１Ｈ，ｍ），３．００−２．９５（１Ｈ，ｍ），２．６７（１Ｈ，ｄｄ），１．２８（３Ｈ，ｄｄ） Production Example 1-11: Production of compound represented by formula (1-11) <Production of compound represented by formula 9-8>

At room temperature, 5 g of the compound represented by the formula (10-1) and 15 ml of tetrahydrofuran were mixed and stirred. The resulting mixture was cooled to 0 ° C., and then 2.6 g of methacrolein and 0.1 g of triethylamine were added dropwise thereto. did. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 6.9 g of a compound represented by the formula (9-8).
1H NMR (CDCl ₃ )
δ ppm: 9.69 (1H, s), 7.53 (2H, d), 7.40 (2H, d), 3.42-3.35 (1H, m), 3.00-2.95 (1H, m), 2.67 (1H, dd), 1.28 (3H, dd)

室温にて、式（９−８）で示される化合物６．９ｇおよびトリフェニルホスフィンアセチルメチレン１０ｇをクロロホルム５０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−８）で示される化合物５．３ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５２（２Ｈ，ｄ），７．３６（２Ｈ，ｄ），６．７２（１Ｈ，ｄｄ），６．０９（１Ｈ，ｄｄ），３．０３（２Ｈ，ｄｄｄ），２．６７（１Ｈ，ｄｔ），２．２４（３Ｈ，ｓ），１．２５（３Ｈ，ｄ） <Production of Compound represented by Formula 7-8>

At room temperature, 6.9 g of the compound represented by the formula (9-8) and 10 g of triphenylphosphine acetylmethylene were dissolved in 50 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 5.3 g of a compound represented by the formula (7-8).
1H NMR (CDCl ₃ )
δ ppm: 7.52 (2H, d), 7.36 (2H, d), 6.72 (1H, dd), 6.09 (1H, dd), 3.03 (2H, ddd), 2. 67 (1H, dt), 2.24 (3H, s), 1.25 (3H, d)

室温にて、２８％ナトリウムメトキシドメタノール溶液３．９ｇおよび式（８−１）で示される化合物２．７ｇをテトラヒドロフラン６０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−８）で示される化合物５．３ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、ヘキサンを加えた。その後、反応液を氷冷し、析出した結晶をろ過により集め、ヘキサンでよく洗浄し、式（６−８）で示される化合物４．４ｇを得た。
引き続き、室温にて、式（６−８）で示される化合物１．６ｇを水３０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム１．３ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、（２−８）で示される化合物１．３ｇを得た。
１Ｈ ＮＭＲ （ｄ−ＤＭＳＯ）
δ ｐｐｍ：７．５２（２Ｈ，ｔ），７．３５（２Ｈ，ｄ），５．５１（１Ｈ，ｓ），３．４２(１Ｈ，ｓ)，３．０９−２．８２（２Ｈ，ｍ），２．６７(１Ｈ，ｄ)，２．４６（２Ｈ，ｄｔ），２．２５（２Ｈ，ｄｄｄ），１．９０−１．８４（１Ｈ，ｍ），１．０９（３Ｈ，ｄｄ） <Production of compound represented by formula 2-8>

At room temperature, 3.9 g of 28% sodium methoxide methanol solution and 2.7 g of the compound represented by the formula (8-1) were dissolved in 60 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 5.3 g of the compound represented by the formula (7-8) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The resulting reaction solution was cooled to room temperature and hexane was added. Thereafter, the reaction solution was ice-cooled, and the precipitated crystals were collected by filtration and washed thoroughly with hexane to obtain 4.4 g of a compound represented by the formula (6-8).
Subsequently, 1.6 g of the compound represented by the formula (6-8) was dissolved in 30 ml of water at room temperature. To the resulting solution was added anhydrous sodium carbonate 1.3g. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure to obtain 1.3 g of the compound represented by (2-8).
1H NMR (d-DMSO)
δ ppm: 7.52 (2H, t), 7.35 (2H, d), 5.51 (1H, s), 3.42 (1H, s), 3.09-2.82 (2H, m ), 2.67 (1H, d), 2.46 (2H, dt), 2.25 (2H, ddd), 1.90-1.84 (1H, m), 1.09 (3H, dd)

窒素雰囲気下、室温にて、式（２−８）で示される化合物５７０ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−１１）で示される化合物４８０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５３（２Ｈ，ｄ），７．３８（２Ｈ，ｄ），６．９８（２Ｈ，ｓ），５．５４（１Ｈ，ｓ），３．２２―３．１４（１Ｈ，ｍ），２．８７（１Ｈ，ｄｄｄ），２．６７−２．２３（１２Ｈ，ｍ），１．９５−１．８８（１Ｈ，ｍ），１．１６(３Ｈ，ｄｄ)，１．１１−１．０４（６Ｈ，ｍ）
<Production of compound represented by formula 1-11>

Under a nitrogen atmosphere, at room temperature, 570 mg of the compound represented by the formula (2-8) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 480 mg of a compound represented by the formula (1-11).
1H NMR (CDCl ₃ )
δ ppm: 7.53 (2H, d), 7.38 (2H, d), 6.98 (2H, s), 5.54 (1H, s), 3.22-3.14 (1H, m ), 2.87 (1H, ddd), 2.67-2.23 (12H, m), 1.95-1.88 (1H, m), 1.16 (3H, dd), 1.11. 1.04 (6H, m)

フラスコに窒素雰囲気下、室温にて、式（２−８）で示される化合物６００ｍｇおよびジメチルアミノピリジン１．１ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−２）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−１２）で示される化合物５４０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５３（２Ｈ，ｄ），７．３８（２Ｈ，ｄ），６．９４（２Ｈ，ｓ），５．５６（１Ｈ，ｓ），３．１６（１Ｈ，ｄｄｄ），２．８７（１Ｈ，ｄｄｄ），２．６５−２．２５（８Ｈ，ｍ），２．０８(３Ｈ，ｄ)，２．０１（３Ｈ，ｓ），１．９０（１Ｈ，ｔｄ），１．１５（３Ｈ，ｄｄ）
Production Example 1-12: Production of compound represented by formula (1-12) <Production of compound represented by formula 1-12>

In a flask, under a nitrogen atmosphere, at room temperature, 600 mg of the compound represented by the formula (2-8) and 1.1 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-2) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 540 mg of a compound represented by the formula (1-12).
1H NMR (CDCl ₃ )
δ ppm: 7.53 (2H, d), 7.38 (2H, d), 6.94 (2H, s), 5.56 (1H, s), 3.16 (1H, ddd), 2. 87 (1H, ddd), 2.65-2.25 (8H, m), 2.08 (3H, d), 2.01 (3H, s), 1.90 (1H, td), 1.15 (3H, dd)

This invention compound manufactured according to manufacture example 1-12 is shown below.
<Compound represented by Formula 1-162>
1H NMR (CDCl ₃ )
δ ppm: 7.28-7.22 (1H, m), 7.09 (1H, d), 7.03 (1H, dt), 6.93 (2H, s), 6.90-6.85 (1H, m), 5.73 (1H, s), 3.10 (1H, s), 2.83 (1H, dt), 2.60-2.22 (8H, m), 2.06- 1.97 (6H, m), 1.86 (1H, s), 1.13 (3H, d)

室温にて、式（１０−２）で示される化合物５ｇおよびテトラヒドロフラン１５ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこにメタクロレイン２．６ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水洗し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−９）で示される化合物６．３ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．７２（１Ｈ，ｓ），８．６６(１Ｈ，ｓ)，７．６６（１Ｈ，ｄ），７．２７（１Ｈ，ｄ），３．５６（１Ｈ，ｄｄｄ），３．３８−３．３１（１Ｈ，ｍ），２．８４（１Ｈ，ｄｄ），１．２７−１．２５（３Ｈ，ｍ） Production Example 1-13: Production of compound represented by formula (1-13) <Production of compound represented by formula 9-9>

At room temperature, 5 g of the compound represented by formula (10-2) and 15 ml of tetrahydrofuran were mixed and stirred, and the resulting mixture was cooled to 0 ° C., and then 2.6 g of methacrolein and 0.1 g of triethylamine were added dropwise thereto. did. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 6.3 g of a compound represented by the formula (9-9).
1H NMR (CDCl ₃ )
δ ppm: 9.72 (1H, s), 8.66 (1H, s), 7.66 (1H, d), 7.27 (1H, d), 3.56 (1H, ddd), 3. 38-3.31 (1H, m), 2.84 (1H, dd), 1.27-1.25 (3H, m)

室温にて、式（９−９）で示される化合物６．６ｇおよびトリフェニルホスフィンアセチルメチレン９ｇをクロロホルム４０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−９）で示される化合物２．８ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６６(１Ｈ，ｓ)，７．６７−７．６５（１Ｈ，ｍ），７．２８（１Ｈ，ｄ），６．７７（１Ｈ，ｄｄ），６．１０（１Ｈ，ｄｄ），３．３２（２Ｈ，ｄｄｄ），２．７９−２．７２（１Ｈ，ｍ），２．２２（３Ｈ，ｓ），１．２５（３Ｈ，ｄ） <Production of Compound represented by Formula 7-9>

At room temperature, 6.6 g of the compound represented by the formula (9-9) and 9 g of triphenylphosphine acetylmethylene were dissolved in 40 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 2.8 g of a compound represented by the formula (7-9).
1H NMR (CDCl ₃ )
δ ppm: 8.66 (1H, s), 7.67-7.65 (1H, m), 7.28 (1H, d), 6.77 (1H, dd), 6.10 (1H, dd) ), 3.32 (2H, ddd), 2.79-2.72 (1H, m), 2.22 (3H, s), 1.25 (3H, d)

室温にて、２８％ナトリウムメトキシドメタノール溶液２．１ｇおよび式（８−１）で示される化合物１．４ｇをテトラヒドロフラン４０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−９）で示される化合物２．８ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、ヘキサンを加えた。その後、反応液を氷冷し、析出した結晶をろ過により集め、ヘキサンでよく洗浄し、式（６−９）で示される化合物２．０ｇを得た。
引き続き、フラスコに室温にて、式（６−９）で示される化合物１．８ｇを水２５ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム１．５ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、式（２−９）で示される化合物１．３ｇを得た。
１Ｈ ＮＭＲ （ＣＤＣｌ₃）
δ ｐｐｍ：８．６６（１Ｈ，ｓ），７．６７−７．６４（１Ｈ，ｍ），７．２５−７．１９（１Ｈ，ｍ），５．５２（１Ｈ，ｓ），３．４９−３．４１（１Ｈ，ｍ），３．０５−２．９６（１Ｈ，ｍ），２．７５（１Ｈ，ｄｄ），２．５８−２．４５（２Ｈ，ｍ），２．３７−２．１８（２Ｈ，ｍ），１．９８−１．８８（１Ｈ，ｍ），１．０６（３Ｈ，ｄｄ） <Production of compound represented by formula 2-9>

At room temperature, 2.1 g of 28% sodium methoxide methanol solution and 1.4 g of the compound represented by the formula (8-1) were dissolved in 40 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 2.8 g of the compound represented by the formula (7-9) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The resulting reaction solution was cooled to room temperature and hexane was added. Thereafter, the reaction solution was ice-cooled, and the precipitated crystals were collected by filtration and washed thoroughly with hexane to obtain 2.0 g of a compound represented by the formula (6-9).
Subsequently, 1.8 g of the compound represented by the formula (6-9) was dissolved in 25 ml of water at room temperature in the flask. 1.5 g of anhydrous sodium carbonate was added to the resulting solution. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure to obtain 1.3 g of a compound represented by the formula (2-9).
1H NMR (CDCl ₃ )
δ ppm: 8.66 (1H, s), 7.67-7.64 (1H, m), 7.25-7.19 (1H, m), 5.52 (1H, s), 3.49 -3.41 (1H, m), 3.05-2.96 (1H, m), 2.75 (1H, dd), 2.58-2.45 (2H, m), 2.37-2 .18 (2H, m), 1.98-1.88 (1H, m), 1.06 (3H, dd)

窒素雰囲気下、室温にて、式（２−９）で示される化合物５７０ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−１３）で示される化合物５７０ｍｇを得た。得られた式（１−１３）で示される化合物をキラルカラム（ＣＨＩＲＡＬＰＡＫ（登録商標） ＩＣ−３（ダイセル社製）、４．６ｘ２５０ｍｍ、３μｍ、検出器：２５４ｎｍ）を用い、カラム温度４０度、移動相の流速：ＣＯ₂ ２．０ｍｌ／ｍｉｎ、ＭｅＯＨ０．１５ｍｌ／ｍｉn、背圧：１５MPaの条件に付し、保持時間１３ ｍｉｎのピーク（以下１−１３−Ａとする。）と１６ ｍｉｎ（以下１−１３−Ｂとする。）のピークに分離した。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６７（１Ｈ，ｓ），７．６６（１Ｈ，ｄｄ），７．２８(１Ｈ，ｄ)，６．９８（２Ｈ，ｓ），５．５４（１Ｈ，ｓ），３．５９（１Ｈ，ｄｄｄ），３．０２(１Ｈ，ｄｄｄｄ)，２．７６−２．２６（１２Ｈ，ｍ），１．９５（１Ｈ，ｔ），１．１５(３Ｈ，ｄｔ)，１．０９−１．０２（６Ｈ，ｍ） <Production of Compound represented by Formula 1-13>

Under a nitrogen atmosphere, at room temperature, 570 mg of the compound represented by the formula (2-9) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 570 mg of a compound represented by the formula (1-13). Using the obtained compound represented by the formula (1-13) using a chiral column (CHIRALPAK (registered trademark) IC-3 (manufactured by Daicel), 4.6 × 250 mm, 3 μm, detector: 254 nm), the column temperature was 40 ° C. Phase flow rate: CO ₂ 2.0 ml / min, MeOH 0.15 ml / min, back pressure: 15 MPa, with a retention time of 13 min peak (hereinafter referred to as 1-13-A) and 16 min (hereinafter referred to as “13-A”). 1-13-B).
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, s), 7.66 (1H, dd), 7.28 (1H, d), 6.98 (2H, s), 5.54 (1H, s), 3. 59 (1H, ddd), 3.02 (1H, dddd), 2.76-2.26 (12H, m), 1.95 (1H, t), 1.15 (3H, dt), 1.09 -1.02 (6H, m)

窒素雰囲気下、室温にて、式（２−９）で示される化合物４５０ｍｇおよびジメチルアミノピリジン６００ｍｇをクロロホルム２．５ｍｌとトルエン０．５ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−２）で示される化合物５００ｍｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１−１４）で示される化合物３２０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６６（１Ｈ，ｓ），７．６６（１Ｈ，ｄｄ），７．２７(１Ｈ，ｄ)，６．９３（２Ｈ，ｓ），５．６５（１Ｈ，ｓ），３．５７（１Ｈ，ｄｄｄ），３．０７−２．９６（１Ｈ，ｍ），２．７４−２．２７（６Ｈ，ｍ），２．０７−１．９４（９Ｈ，ｍ），１．１７−１．１０（３Ｈ，ｍ） Production Example 1-14: Production of compound represented by formula (1-14) <Production of compound represented by formula 1-14>

Under a nitrogen atmosphere, at room temperature, 450 mg of the compound represented by formula (2-9) and 600 mg of dimethylaminopyridine were dissolved in a mixture of 2.5 ml of chloroform and 0.5 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 500 mg of the compound represented by the formula (3-2) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 320 mg of the compound represented by the formula (1-14).
1H NMR (CDCl ₃ )
δ ppm: 8.66 (1H, s), 7.66 (1H, dd), 7.27 (1H, d), 6.93 (2H, s), 5.65 (1H, s), 3. 57 (1H, ddd), 3.07-2.96 (1H, m), 2.74-2.27 (6H, m), 2.07-1.94 (9H, m), 1.17- 1.10 (3H, m)

室温にて、式（１０−１）で示される化合物３ｇおよびテトラヒドロフラン１０ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこにクロトンアルデヒド１．５ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水洗し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−１０）で示される化合物４．４ｇを得た。
引き続き、室温にて、式（９−１０）で示される化合物４．４ｇおよびトリフェニルホスフィンアセチルメチレン６．２ｇをクロロホルム２５ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−１０）で示される化合物３．７ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５４（２Ｈ，ｄ），７．４５（２Ｈ，ｄ），６．７９（１Ｈ，ｄｔ），６．１４−６．１０（１Ｈ，ｍ），３．５１（１Ｈ，ｑ），２．６０−２．４５（２Ｈ，ｍ），２．２４（３Ｈ，ｓ），１．３６（３Ｈ，ｄ） Production Example 1-15: Production of compound represented by formula (1-15) <Production of compound represented by formula 7-10>

At room temperature, 3 g of the compound represented by the formula (10-1) and 10 ml of tetrahydrofuran were mixed and stirred, and the resulting mixture was cooled to 0 ° C., and then 1.5 g of crotonaldehyde and 0.1 g of triethylamine were added dropwise thereto. did. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 4.4 g of a compound represented by the formula (9-10).
Subsequently, at room temperature, 4.4 g of the compound represented by the formula (9-10) and 6.2 g of triphenylphosphine acetylmethylene were dissolved in 25 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 3.7 g of a compound represented by the formula (7-10).
1H NMR (CDCl ₃ )
δ ppm: 7.54 (2H, d), 7.45 (2H, d), 6.79 (1H, dt), 6.14-6.10 (1H, m), 3.51 (1H, q ), 2.60-2.45 (2H, m), 2.24 (3H, s), 1.36 (3H, d)

室温にて、２８％ナトリウムメトキシドメタノール溶液２．７ｇおよび式（８−１）で示される化合物１．８ｇをテトラヒドロフラン４０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−１０）で示される化合物３．７ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、ヘキサンを加えた。その後、反応液を氷冷し、析出した結晶をろ過により集め、ヘキサンでよく洗浄し、式（６−１０）で示される化合物２．９ｇを得た。
引き続き、室温にて、式（６−１０）で示される化合物２．９ｇを水４０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム２．３ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、式（２−１０）で示される化合物２．１ｇを得た。
１Ｈ ＮＭＲ （ＣＤＣｌ₃）
δ ｐｐｍ：７．５４（２Ｈ，ｔ），７．４２（２Ｈ，ｄｄ），５．４８（１Ｈ，ｓ），３．３６（２Ｈ，ｔｔ），２．７８(２Ｈ，ｄ)，２．５３−２．３４（２Ｈ，ｍ），２．１３（１Ｈ，ｄｄ），１．７５−１．５３（２Ｈ，ｍ），１．３４−１．２９（３Ｈ，ｍ） <Production of compound represented by formula 2-10>

At room temperature, 2.7 g of 28% sodium methoxide methanol solution and 1.8 g of the compound represented by the formula (8-1) were dissolved in 40 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 3.7 g of the compound represented by the formula (7-10) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The resulting reaction solution was cooled to room temperature and hexane was added. Thereafter, the reaction solution was ice-cooled, and the precipitated crystals were collected by filtration and washed thoroughly with hexane to obtain 2.9 g of a compound represented by the formula (6-10).
Subsequently, 2.9 g of the compound represented by the formula (6-10) was dissolved in 40 ml of water at room temperature. To the resulting solution was added anhydrous sodium carbonate 2.3 g. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure to obtain 2.1 g of a compound represented by formula (2-10).
1H NMR (CDCl ₃ )
δ ppm: 7.54 (2H, t), 7.42 (2H, dd), 5.48 (1H, s), 3.36 (2H, tt), 2.78 (2H, d), 2. 53-2.34 (2H, m), 2.13 (1H, dd), 1.75-1.53 (2H, m), 1.34-1.29 (3H, m)

窒素雰囲気下、室温にて、式（２−１０）で示される化合物５７０ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−１５）で示される化合物３６０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５６−７．５２（２Ｈ，ｍ），７．４６−７．４１（２Ｈ，ｍ），６．９８（２Ｈ，ｓ），５．５３（１Ｈ，ｓ），３．４９−３．４２（１Ｈ，ｍ），２．７６−２．２３（１２Ｈ，ｍ），１．８３−１．７１（２Ｈ，ｍ），１．３８(３Ｈ，ｄｄ)，１．０６（６Ｈ，ｔｔ） <Production of compound represented by formula 1-15>

Under a nitrogen atmosphere, at room temperature, 570 mg of the compound represented by the formula (2-10) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 360 mg of the compound represented by the formula (1-15).
1H NMR (CDCl ₃ )
δ ppm: 7.56-7.52 (2H, m), 7.46-7.41 (2H, m), 6.98 (2H, s), 5.53 (1H, s), 3.49 -3.42 (1H, m), 2.76-2.23 (12H, m), 1.83-1.71 (2H, m), 1.38 (3H, dd), 1.06 (6H) , Tt)

室温にて、式（１０−８）で示される化合物２ｇおよびテトラヒドロフラン１０ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこに９５％アクロレイン０．８ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水洗し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−１１）で示される化合物２．５ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．８４（１Ｈ，ｓ），８．５９（１Ｈ，ｓ），７．７６（１Ｈ，ｓ），３．４９（２Ｈ，ｔ），２．９６（２Ｈ，ｔ） Production Example 1-16: Production of compound represented by formula (1-16) <Production of compound represented by formula 9-11>

At room temperature, 2 g of the compound represented by the formula (10-8) and 10 ml of tetrahydrofuran were mixed and stirred, and the resulting mixture was cooled to 0 ° C. Then, 0.8 g of 95% acrolein and 0.1 g of triethylamine were added thereto. It was dripped. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 2.5 g of a compound represented by the formula (9-11).
1H NMR (CDCl ₃ )
δ ppm: 9.84 (1H, s), 8.59 (1H, s), 7.76 (1H, s), 3.49 (2H, t), 2.96 (2H, t)

室温にて、式（９−１１）で示される化合物２．５ｇおよびトリフェニルホスフィンアセチルメチレン３．４ｇをクロロホルム１５ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−１１）で示される化合物１．２ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６０（１Ｈ，ｓ），７．７６（１Ｈ，ｓ），６．８４（１Ｈ，ｄｔ），６．１６（１Ｈ，ｄｔ），３．３６（２Ｈ，ｔ），２．６８（２Ｈ，ｄｄｄ），２．２６（３Ｈ，ｓ） <Production of Compound represented by Formula 7-11>

At room temperature, 2.5 g of the compound represented by the formula (9-11) and 3.4 g of triphenylphosphine acetylmethylene were dissolved in 15 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 1.2 g of a compound represented by the formula (7-11).
1H NMR (CDCl ₃ )
δ ppm: 8.60 (1H, s), 7.76 (1H, s), 6.84 (1H, dt), 6.16 (1H, dt), 3.36 (2H, t), 2. 68 (2H, ddd), 2.26 (3H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液０．８ｇおよび式（８−１）で示される化合物０．５６ｇをテトラヒドロフラン１５ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−１１）で示される化合物１．２ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−１１）で示される化合物０．８ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：８．８１（１Ｈ，ｓ），８．３４（１Ｈ，ｓ），４．３８（１Ｈ，ｓ），３．５０（３Ｈ，ｓ），３．４２−３．２５（１Ｈ，ｍ），３．１５−３．０７（１Ｈ，ｍ），２．８２（１Ｈ，ｄ），２．３３−２．２３（１Ｈ，ｍ），２．１２（１Ｈ，ｄｄ），１．７９（１Ｈ，ｄｔ），１．６３−１．５０（２Ｈ，ｍ） <Production of Compound represented by Formula 6-11>

At room temperature, 0.8 g of 28% sodium methoxide methanol solution and 0.56 g of the compound represented by the formula (8-1) were dissolved in 15 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 1.2 g of the compound represented by the formula (7-11) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The obtained reaction liquid was cooled to room temperature, and the precipitated crystals were collected by filtration and washed well with tert-butyl methyl ether and hexane in order to obtain 0.8 g of a compound represented by the formula (6-11).
1H NMR (d-DMSO)
δ ppm: 8.81 (1H, s), 8.34 (1H, s), 4.38 (1H, s), 3.50 (3H, s), 3.42-3.25 (1H, m ), 3.15-3.07 (1H, m), 2.82 (1H, d), 2.33-2.23 (1H, m), 2.12 (1H, dd), 1.79 ( 1H, dt), 1.63-1.50 (2H, m)

フラスコに室温にて、式（６−１１）で示される化合物０．８ｇを水１０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム０．６ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−１１）で示される化合物０．６ｇを得た。
１Ｈ ＮＭＲ （ｄ−ＤＭＳＯ）
δ ｐｐｍ：１１．０６（１Ｈ，ｓ），８．８１（１Ｈ，ｄ），８．３５（１Ｈ，ｄ），５．２０（１Ｈ，ｓ），３．２７（２Ｈ，ｔ），２．５１−１．９１（５Ｈ，ｍ），１．７４（２Ｈ，ｄ） <Production of compound represented by formula 2-11>

In a flask, 0.8 g of the compound represented by the formula (6-11) was dissolved in 10 ml of water at room temperature. 0.6 g of anhydrous sodium carbonate was added to the resulting solution. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 0.6 g of a compound represented by the formula (2-11).
1H NMR (d-DMSO)
δ ppm: 11.06 (1H, s), 8.81 (1H, d), 8.35 (1H, d), 5.20 (1H, s), 3.27 (2H, t), 2. 51-1.91 (5H, m), 1.74 (2H, d)

窒素雰囲気下、室温にて、式（２−１１）で示される化合物６００ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−１６）で示される化合物３６０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６０(１Ｈ，ｓ)，７．７５（１Ｈ，ｄ），６．９７（２Ｈ，ｓ），５．７１（１Ｈ，ｓ），３．３１（２Ｈ，ｄｄｄ），２．７５（２Ｈ，ｔ），２．５１−２．２３（１０Ｈ，ｍ），１．９４−１．８８（２Ｈ，ｍ），１．０９−１．００（６Ｈ，ｍ） <Production of compound represented by formula 1-16>

Under a nitrogen atmosphere, at room temperature, 600 mg of the compound represented by the formula (2-11) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 360 mg of the compound represented by the formula (1-16).
1H NMR (CDCl ₃ )
δ ppm: 8.60 (1H, s), 7.75 (1H, d), 6.97 (2H, s), 5.71 (1H, s), 3.31 (2H, ddd), 2. 75 (2H, t), 2.51-2.23 (10H, m), 1.94-1.88 (2H, m), 1.09-1.00 (6H, m)

室温にて、式（９−１２）で示される化合物９．３ｇおよびトリフェニルホスフィンアセチルメチレン２２ｇをクロロホルム９０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−１２）で示される化合物２．１ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３１−７．２３（２Ｈ，ｍ），６．９５（１Ｈ，ｔｔ），６．９２−６．８２（３Ｈ，ｍ），６．２１−６．１４（１Ｈ，ｍ），４．０９（２Ｈ，ｔ），２．６９（２Ｈ，ｑ），２．２４（３Ｈ，ｓ） Production Example 1-17: Production of compound represented by formula (1-17) <Production of compound represented by formula 7-12>

At room temperature, 9.3 g of the compound represented by the formula (9-12) and 22 g of triphenylphosphine acetylmethylene were dissolved in 90 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 2.1 g of a compound represented by the formula (7-12).
1H NMR (CDCl ₃ )
δ ppm: 7.31-7.23 (2H, m), 6.95 (1H, tt), 6.92-6.82 (3H, m), 6.21-6.14 (1H, m) , 4.09 (2H, t), 2.69 (2H, q), 2.24 (3H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液２．３ｇおよび式（８−１）で示される化合物１．６ｇをテトラヒドロフラン４０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−１２）で示される化合物２．１ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−１２）で示される化合物２．６ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：７．２７（２Ｈ，ｔ），６．９２−６．８９（３Ｈ，ｍ），４．４０（１Ｈ，ｓ），４．３８−３．８９（２Ｈ，ｍ），３．５４（３Ｈ，ｓ），２．８７（１Ｈ，ｄ），２．４０−２．３０（１Ｈ，ｍ），２．０８（１Ｈ，ｄｄ），１．８１（１Ｈ，ｄｄ），１．７２−１．６４（１Ｈ，ｍ），１．６０−１．５１（１Ｈ，ｍ） <Production of compound represented by formula 6-12>

At room temperature, 2.3 g of 28% sodium methoxide methanol solution and 1.6 g of the compound represented by the formula (8-1) were dissolved in 40 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 2.1 g of the compound represented by the formula (7-12) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The resulting reaction liquid was cooled to room temperature, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane to obtain 2.6 g of a compound represented by the formula (6-12).
1H NMR (d-DMSO)
δ ppm: 7.27 (2H, t), 6.92-6.89 (3H, m), 4.40 (1H, s), 4.38-3.89 (2H, m), 3.54 (3H, s), 2.87 (1H, d), 2.40-2.30 (1H, m), 2.08 (1H, dd), 1.81 (1H, dd), 1.72- 1.64 (1H, m), 1.60-1.51 (1H, m)

室温にて、式（６−１２）で示される化合物２．０ｇを水４０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム２．０ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで不純物を洗浄した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶を順次、ｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで洗浄して式（２−１２）で示される化合物１．２ｇを得た。
１Ｈ ＮＭＲ （ｄ−ＤＭＳＯ）
δ ｐｐｍ：１１．０６（１Ｈ，ｓ），７．２８（２Ｈ，ｔ），６．９２（２Ｈ，ｄｄ），５．２０（１Ｈ，ｓ），４．０２(２Ｈ，ｔ)，２．５０−１．９９（５Ｈ，ｍ），１．７９（２Ｈ，ｄ） <Production of Compound represented by Formula 2-12>

At room temperature, 2.0 g of the compound represented by the formula (6-12) was dissolved in 40 ml of water. To the resulting solution, 2.0 g of anhydrous sodium carbonate was added. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether, and then acidified with 2N hydrochloric acid, and the aqueous layer was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 1.2 g of a compound represented by the formula (2-12).
1H NMR (d-DMSO)
δ ppm: 11.06 (1H, s), 7.28 (2H, t), 6.92 (2H, dd), 5.20 (1H, s), 4.02 (2H, t), 2. 50-1.99 (5H, m), 1.79 (2H, d)

窒素雰囲気下、室温にて、式（２−１２）で示される化合物４００ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１−１７）で示される化合物３８０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３２−７．２７（２Ｈ，ｍ），６．９７−６．８９（５Ｈ，ｍ），５．６８（１Ｈ，ｓ），４．１１−４．０６（２Ｈ，ｍ），２．７８−２．６９（２Ｈ，ｍ），２．６０−２．２５（１０Ｈ，ｍ），１．９７（２Ｈ，ｄｄｄ），１．１１−１．０５（６Ｈ，ｍ） <Production of Compound represented by Formula 1-17>

Under a nitrogen atmosphere, at room temperature, 400 mg of the compound represented by the formula (2-12) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 380 mg of a compound represented by the formula (1-17).
1H NMR (CDCl ₃ )
δ ppm: 7.32-7.27 (2H, m), 6.97-6.89 (5H, m), 5.68 (1H, s), 4.11-4.06 (2H, m) , 2.78-2.69 (2H, m), 2.60-2.25 (10H, m), 1.97 (2H, ddd), 1.11-1.05 (6H, m)

室温にて、式（９−１３）で示される化合物３．５ｇおよびトリフェニルホスフィンアセチルメチレン７．５ｇをクロロホルム３０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−１３）で示される化合物１．１ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．１４−７．０９（２Ｈ，ｍ），６．９９−６．９３（２Ｈ，ｍ），６．７９（１Ｈ，ｄｔ），６．０８（１Ｈ，ｄｔ），２．６２（２Ｈ，ｔ），２．２７−２．２０（５Ｈ，ｍ），１．８２−１．７４（２Ｈ，ｍ） Production Example 1-18: Production of compound represented by formula (1-18) <Production of compound represented by formula 7-13>

At room temperature, 3.5 g of the compound represented by the formula (9-13) and 7.5 g of triphenylphosphine acetylmethylene were dissolved in 30 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 1.1 g of a compound represented by the formula (7-13).
1H NMR (CDCl ₃ )
δ ppm: 7.14-7.09 (2H, m), 699-6.93 (2H, m), 6.79 (1H, dt), 6.08 (1H, dt), 2.62 (2H, t), 2.27-2.20 (5H, m), 1.82-1.74 (2H, m)

室温にて、２８％ナトリウムメトキシドメタノール溶液１．１ｇおよび式（８−１）で示される化合物０．８ｇをテトラヒドロフラン２０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−１３）で示される化合物１．１ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−１３）で示される化合物１．０ｇを得た。
引き続き、室温にて、式（６−１３）で示される化合物１．０ｇを水２０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム１．０ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−１３）で示される化合物６５０ｍｇを得た。
１Ｈ ＮＭＲ （ｄ−ＤＭＳＯ）
δ ｐｐｍ：１０．９９（１Ｈ，ｓ），７．２５−７．２１（２Ｈ，ｍ），７．１１−７．０５（２Ｈ，ｍ），５．１８（１Ｈ，ｓ），２．５５(２Ｈ，ｔ)，２．４３−１．９１（５Ｈ，ｍ），１．６１−１．５３（２Ｈ，ｍ），１．３５−１．３２（２Ｈ，ｍ） <Production of Compound represented by Formula 2-13>

At room temperature, 1.1 g of 28% sodium methoxide methanol solution and 0.8 g of the compound represented by the formula (8-1) were dissolved in 20 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 1.1 g of the compound represented by the formula (7-13) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The resulting reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane to obtain 1.0 g of a compound represented by the formula (6-13).
Subsequently, 1.0 g of the compound represented by the formula (6-13) was dissolved in 20 ml of water at room temperature. 1.0 g of anhydrous sodium carbonate was added to the resulting solution. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 650 mg of the compound represented by the formula (2-13).
1H NMR (d-DMSO)
δ ppm: 10.99 (1H, s), 7.25-7.21 (2H, m), 7.11-7.05 (2H, m), 5.18 (1H, s), 2.55 (2H, t), 2.43-1.91 (5H, m), 1.61-1.53 (2H, m), 1.35-1.32 (2H, m)

窒素雰囲気下、室温にて、式（２−１３）で示される化合物４３０ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−１８）で示される化合物４４０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．１５−７．１１（２Ｈ，ｍ），６．９９−６．９３（４Ｈ，ｍ），５．６０（１Ｈ，ｓ），２．６７−２．６１（４Ｈ，ｍ），２．４０−２．１９（１０Ｈ，ｍ），１．７４−１．６６（２Ｈ，ｍ），１．５２−１．４６（２Ｈ，ｍ），１．０８―１．００（６Ｈ，ｍ） <Production of compound represented by formula 1-18>

Under a nitrogen atmosphere, at room temperature, 430 mg of the compound represented by the formula (2-13) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 440 mg of a compound represented by the formula (1-18).
1H NMR (CDCl ₃ )
δ ppm: 7.15-7.11 (2H, m), 699-6.93 (4H, m), 5.60 (1H, s), 2.67-2.61 (4H, m) 2.40-2.19 (10H, m), 1.74-1.66 (2H, m), 1.52-1.46 (2H, m), 1.08-1.00 (6H, m)

室温にて、式（１０−１４）で示される化合物９．０ｇおよびテトラヒドロフラン３０ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこに９５％アクロレイン３．６ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−１４）で示される化合物１１ｇを得た。
引き続き、室温にて、式（９−１４）で示される化合物１１ｇおよびトリフェニルホスフィンアセチルメチレン１５．８ｇをクロロホルム５０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：５）に付し、式（７−１４）で示される化合物２．６５ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：６．７９−６．７１（１Ｈ，ｍ），６．１１（１Ｈ，ｄｔ），３．０２（２Ｈ，ｔｄ），２．５１（２Ｈ，ｄｔ），２．２５（３Ｈ，ｄｄ） Production Example 1-19: Production of compound represented by formula (1-69) <Production of compound represented by formula 7-14>

At room temperature, 9.0 g of the compound represented by the formula (10-14) and 30 ml of tetrahydrofuran were mixed and stirred, and the obtained mixture was cooled to 0 ° C. 1 g was added dropwise. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 11 g of a compound represented by the formula (9-14).
Subsequently, 11 g of the compound represented by formula (9-14) and 15.8 g of triphenylphosphine acetylmethylene were dissolved in 50 ml of chloroform at room temperature. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 5) to obtain 2.65 g of a compound represented by the formula (7-14).
1H NMR (CDCl ₃ )
δ ppm: 6.79-6.71 (1H, m), 6.11 (1H, dt), 3.02 (2H, td), 2.51 (2H, dt), 2.25 (3H, dd) )

室温にて、２８％ナトリウムメトキシドメタノール溶液１．９ｇおよび式（８−１）で示される化合物１．３ｇをテトラヒドロフラン３５ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−１４）で示される化合物２．６５ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−１４）で示される化合物１．１ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：４．３９（１Ｈ，ｓ），３．４９（３Ｈ，ｓ），２．９９−２．９２（１Ｈ, m）、２．８６−２．７６（２Ｈ，ｍ），２．２８−２．１９（１Ｈ，ｍ），２．０５−１．９９（１Ｈ，ｍ），１．７６−１．６５（１Ｈ，ｍ），１．４４−１．３３（２Ｈ，ｍ） <Production of compound represented by formula 6-14>

At room temperature, 1.9 g of 28% sodium methoxide methanol solution and 1.3 g of the compound represented by the formula (8-1) were dissolved in 35 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 2.65 g of the compound represented by the formula (7-14) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The resulting reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane to obtain 1.1 g of the compound represented by the formula (6-14).
1H NMR (d-DMSO)
δ ppm: 4.39 (1H, s), 3.49 (3H, s), 2.99-2.92 (1H, m), 2.86-2.76 (2H, m), 2.28 -2.19 (1H, m), 2.05-1.99 (1H, m), 1.76-1.65 (1H, m), 1.44-1.33 (2H, m)

室温にて、式（６−１４）で示される化合物１．１ｇを水２０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム８４０ｍｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にし、酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−１４）で示される化合物８００ｍｇを得た。
続いて、窒素雰囲気下、室温にて、式（２−１４）で示される化合物５８０ｍｇおよびジメチルアミピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−６９）で示される化合物１５０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：６．９９（２Ｈ，ｓ），５．５６（１Ｈ，ｓ），３．００−２．９５（２Ｈ，ｍ），２．７１−２．６２（２Ｈ，ｍ），２．４７−２．２２（１０Ｈ，ｍ），１．７５（２Ｈ，ｄｄ），１．１０−１．０４（６Ｈ，ｍ） <Production of Compound represented by Formula 1-69>

At room temperature, 1.1 g of the compound represented by the formula (6-14) was dissolved in 20 ml of water. To the resulting solution was added anhydrous sodium carbonate 840 mg. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, acidified with 2N hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 800 mg of the compound represented by the formula (2-14).
Subsequently, 580 mg of the compound represented by the formula (2-14) and 1.05 g of dimethylamipyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene at room temperature under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 150 mg of the compound represented by the formula (1-69).
1H NMR (CDCl ₃ )
δ ppm: 6.99 (2H, s), 5.56 (1H, s), 3.00-2.95 (2H, m), 2.71-2.62 (2H, m), 2.47 -2.22 (10H, m), 1.75 (2H, dd), 1.10-1.04 (6H, m)

室温にて、式（１０−１５）で示される化合物３．３ｇおよびテトラヒドロフラン１５ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこに９５％アクロレイン１．４ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水洗し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−１５）で示される化合物４．２ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．７６（１Ｈ，ｓ），７．５２（２Ｈ，ｄ），７．３７（２Ｈ，ｄ），３．２１−３．１６（２Ｈ，ｍ），２．８０−２．７６（２Ｈ，ｍ） Production Example 1-20: Production of compound represented by formula (1-31) <Production of compound represented by formula 9-15>

At room temperature, 3.3 g of the compound represented by the formula (10-15) and 15 ml of tetrahydrofuran were mixed and stirred, and the resulting mixture was cooled to 0 ° C., and then 1.4 g of 95% acrolein and 0. 1 g was added dropwise. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 4.2 g of a compound represented by the formula (9-15).
1H NMR (CDCl ₃ )
δ ppm: 9.76 (1H, s), 7.52 (2H, d), 7.37 (2H, d), 3.21-3.16 (2H, m), 2.80-2.76 (2H, m)

室温にて、式（９−１５）で示される化合物４．２ｇおよびトリフェニルホスフィンアセチルメチレン６．０ｇをクロロホルム２０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−１５）で示される化合物２．７ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３７（２Ｈ，ｄ），７．１６（２Ｈ，ｄ），６．７７（１Ｈ，ｄｔ），６．０９（１Ｈ，ｄ），３．０４（２Ｈ，ｔ），２．５８−２．５２（２Ｈ，ｍ），２．２３（３Ｈ，ｓ） <Production of Compound represented by Formula 7-15>

At room temperature, 4.2 g of the compound represented by the formula (9-15) and 6.0 g of triphenylphosphine acetylmethylene were dissolved in 20 ml of chloroform. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 2.7 g of a compound represented by the formula (7-15).
1H NMR (CDCl ₃ )
δ ppm: 7.37 (2H, d), 7.16 (2H, d), 6.77 (1H, dt), 6.09 (1H, d), 3.04 (2H, t), 2. 58-2.52 (2H, m), 2.23 (3H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液２ｇおよび式（８−１）で示される化合物１．４ｇをテトラヒドロフラン４０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−１５）で示される化合物２．７ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−１５）で示される化合物１．８ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：７．３９（２Ｈ，ｄ），７．３１（２Ｈ，ｄ），４．４０（１Ｈ，ｓ），３．４７（３Ｈ，ｓ），３．０７−３．０１（１Ｈ，ｍ），２．９２−２．８０（２Ｈ，ｍ），２．３４−２．２４（１Ｈ，ｍ），２．０９（１Ｈ，ｄｄ），１．７５（１Ｈ，ｄｄ），１．５１−１．４０（２Ｈ，ｍ） <Production of compound represented by formula 6-15>

At room temperature, 2 g of 28% sodium methoxide methanol solution and 1.4 g of the compound represented by the formula (8-1) were dissolved in 40 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 2.7 g of the compound represented by the formula (7-15) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The obtained reaction liquid was cooled to room temperature, and the precipitated crystals were collected by filtration and washed well with tert-butyl methyl ether and hexane in order to obtain 1.8 g of a compound represented by the formula (6-15).
1H NMR (d-DMSO)
δ ppm: 7.39 (2H, d), 7.31 (2H, d), 4.40 (1H, s), 3.47 (3H, s), 3.07-3.01 (1H, m ), 2.92-2.80 (2H, m), 2.34-2-24 (1H, m), 2.09 (1H, dd), 1.75 (1H, dd), 1.51- 1.40 (2H, m)

室温にて、式（６−１５）で示される化合物１．８ｇを水３５ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム１．４ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にし、酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−１５）で示される化合物１．６ｇを得た。
続いて、窒素雰囲気下、室温にて、式（２−１５）で示される化合物５７０ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−３１）で示される化合物２９０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３６（２Ｈ，ｄ），７．１５（２Ｈ，ｄ），６．９８（２Ｈ，ｓ），５．５９（１Ｈ，ｓ），３．００（２Ｈ，ｄｄｄ），２．７１−２．６５（２Ｈ，ｍ），２．４８−２．２２（１０Ｈ，ｍ），１．８３（２Ｈ，ｑ），１．１０−１．０３（６Ｈ，ｍ） <Production of compound represented by formula 1-31>

At room temperature, 1.8 g of the compound represented by formula (6-15) was dissolved in 35 ml of water. 1.4 g of anhydrous sodium carbonate was added to the resulting solution. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, acidified with 2N hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 1.6 g of a compound represented by the formula (2-15).
Subsequently, 570 mg of the compound represented by the formula (2-15) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene at room temperature under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 290 mg of a compound represented by the formula (1-31).
1H NMR (CDCl ₃ )
δ ppm: 7.36 (2H, d), 7.15 (2H, d), 6.98 (2H, s), 5.59 (1H, s), 3.00 (2H, ddd), 2. 71-2.65 (2H, m), 2.48-2.22 (10H, m), 1.83 (2H, q), 1.10-1.03 (6H, m)

室温にて、式（１０−１６）で示される化合物５．０ｇおよびテトラヒドロフラン３０ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこに９５％アクロレイン２．８ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−１６）で示される化合物６．７ｇを得た。
引き続き、室温にて、式（９−１６）で示される化合物６．７ｇおよびトリフェニルホスフィンアセチルメチレン１１．２ｇをクロロホルム４０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（７−１６）で示される化合物５．０ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．２３(１Ｈ，ｄ），８．２５−８．２１(１Ｈ，ｍ），７．３２−７．２８（１Ｈ，ｍ），６．８３（１Ｈ，ｄｔ），６．１６（１Ｈ，ｄ），３．４１（２Ｈ，ｔ），２．７２−２．６７（２Ｈ，ｍ），２．２４（３Ｈ，ｓ） Production Example 1-21: Production of compound represented by formula (1-73) <Production of compound represented by formula 7-16>

At room temperature, 5.0 g of the compound represented by the formula (10-16) and 30 ml of tetrahydrofuran were mixed and stirred. The resulting mixture was cooled to 0 ° C., and then 2.8 g of 95% acrolein and 0.81 of triethylamine were added thereto. 1 g was added dropwise. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 6.7 g of a compound represented by the formula (9-16).
Subsequently, 6.7 g of the compound represented by the formula (9-16) and 11.2 g of triphenylphosphine acetylmethylene were dissolved in 40 ml of chloroform at room temperature. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 5.0 g of a compound represented by the formula (7-16).
1H NMR (CDCl ₃ )
δ ppm: 9.23 (1H, d), 8.25-8.21 (1H, m), 7.32-7.28 (1H, m), 6.83 (1H, dt), 6.16 (1H, d), 3.41 (2H, t), 2.72-2.67 (2H, m), 2.24 (3H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液４．２ｇおよび式（８−１）で示される化合物２．９ｇをテトラヒドロフラン８０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−１６）で示される化合物５．０ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−１６）で示される化合物４．９ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：９．２１(１Ｈ，ｄ），８．３６(１Ｈ，ｄｄ），７．５４（１Ｈ，ｄｄ），４．３８（１Ｈ，ｓ），３．５２（３Ｈ，ｓ），３．３４−２．８２（３Ｈ，ｍ）、２．３３−２．２４（１Ｈ，ｍ），２．１６−２．１１（１Ｈ，ｍ），１．８３−１．７４（１Ｈ，ｍ），１．６１−１．５３（２Ｈ，ｍ） <Production of compound represented by formula 6-14>

At room temperature, 4.2 g of 28% sodium methoxide methanol solution and 2.9 g of the compound represented by the formula (8-1) were dissolved in 80 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 5.0 g of the compound represented by the formula (7-16) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The obtained reaction liquid was cooled to room temperature, and the precipitated crystals were collected by filtration and washed well with tert-butyl methyl ether and hexane in order to obtain 4.9 g of a compound represented by the formula (6-16).
1H NMR (d-DMSO)
δ ppm: 9.21 (1H, d), 8.36 (1H, dd), 7.54 (1H, dd), 4.38 (1H, s), 3.52 (3H, s), 3. 34-2.82 (3H, m), 2.33-2.24 (1H, m), 2.16-2.11 (1H, m), 1.83-1.74 (1H, m), 1.61-1.53 (2H, m)

室温にて、式（６−１６）で示される化合物３．０ｇを水６５ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム２．７ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−１６）で示される化合物１．１ｇを得た。
続いて、窒素雰囲気下、室温にて、式（２−１６）で示される化合物５００ｍｇおよびジメチルアミピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝２：３）に付し、式（１−７３）で示される化合物５０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．２５（１Ｈ，ｄ），８．２３（１Ｈ，ｄｔ），７．３０（１Ｈ，ｄ），６．９８（２Ｈ，ｓ），５．５８（１Ｈ，ｓ），３．３６（２Ｈ，ｔ），２．８０−２．７１（２Ｈ，ｍ），２．５２−２．２５（１０Ｈ，ｍ），１．９６−１．９０（２Ｈ，ｍ），１．０９−１．０３（６Ｈ，ｍ） <Production of Compound represented by Formula 1-73>

At room temperature, 3.0 g of the compound represented by the formula (6-16) was dissolved in 65 ml of water. To the resulting solution was added 2.7 g of anhydrous sodium carbonate. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 1.1 g of a compound represented by the formula (2-16).
Subsequently, 500 mg of the compound represented by the formula (2-16) and 1.05 g of dimethylamipyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene at room temperature under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 2: 3) to obtain 50 mg of the compound represented by the formula (1-73).
1H NMR (CDCl ₃ )
δ ppm: 9.25 (1H, d), 8.23 (1H, dt), 7.30 (1H, d), 6.98 (2H, s), 5.58 (1H, s), 3. 36 (2H, t), 2.80-2.71 (2H, m), 2.52-2.25 (10H, m), 1.96-1.90 (2H, m), 1.09- 1.03 (6H, m)

室温にて、式（１０−２）で示される化合物３．０ｇおよびテトラヒドロフラン１５ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこに２−エチルアクロレイン１．８５ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下１．５時間攪拌した。その後、得られた混合物を水に加えた。得られた混合物をｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−１７）で示される化合物４．３ｇを得た。
引き続き、室温にて、式（９−１７）で示される化合物４．３ｇおよびトリフェニルホスフィンアセチルメチレン５．８ｇをクロロホルム２０ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−１７）で示される化合物１．１ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６６(１Ｈ，ｓ），７．６７−７．６４(１Ｈ，ｍ)，７．２８−７．２４（１Ｈ，ｍ），６．６６−６．５９（１Ｈ，ｍ），６．１０（１Ｈ，ｄｄ），３．４５−３．２４（２Ｈ，ｍ），２．５３−２．４７（１Ｈ，ｍ），２．２０（３Ｈ，ｓ），１．７９−１．４６（２Ｈ，ｍ）、０．９６−０．９２（３Ｈ，ｍ） Production Example 1-22: Production of compound represented by formula (1-74) <Production of compound represented by formula 7-17>

At room temperature, 3.0 g of the compound represented by the formula (10-2) and 15 ml of tetrahydrofuran were mixed and stirred, and the resulting mixture was cooled to 0 ° C. Then, 1.85 g of 2-ethylacrolein and triethylamine 0 were added thereto. 0.1 g was added dropwise. The resulting mixture was stirred for 1.5 hours under ice cooling. The resulting mixture was then added to water. The resulting mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 4.3 g of a compound represented by the formula (9-17).
Subsequently, 4.3 g of the compound represented by the formula (9-17) and 5.8 g of triphenylphosphine acetylmethylene were dissolved in 20 ml of chloroform at room temperature. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oil was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 1.1 g of a compound represented by the formula (7-17).
1H NMR (CDCl ₃ )
δ ppm: 8.66 (1H, s), 7.67-7.64 (1H, m), 7.28-7.24 (1H, m), 6.66-6.59 (1H, m) 6.10 (1H, dd), 3.45-3.24 (2H, m), 2.53-2.47 (1H, m), 2.20 (3H, s), 1.79-1 .46 (2H, m), 0.96-0.92 (3H, m)

室温にて、２８％ナトリウムメトキシドメタノール溶液８１０ｍｇおよび式（８−１）で示される化合物５６０ｍｇをテトラヒドロフラン１５ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−１７）で示される化合物１．１ｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−１７）で示される化合物１．６ｇを得た。
引き続き、室温にて、式（６−１７）で示される化合物１．６ｇを水３０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム１．２ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にし、酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−１７）で示される化合物１．２ｇを得た。
続いて、窒素雰囲気下、室温にて、式（２−１７）で示される化合物６００ｍｇおよびジメチルアミピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：５）に付し、式（１−７４）で示される化合物２００ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６７（１Ｈ，ｓ），７．６６（１Ｈ，ｄｄ），７．２７（１Ｈ，ｄ），６．９８（２Ｈ，ｓ），５．５２（１Ｈ，ｓ），３．５７−３．４６（１Ｈ，ｍ），３．３１−３．１７（１Ｈ，ｍ），２．７１−２．５８（３Ｈ，ｍ），２．４４−２．２５（１０Ｈ，ｍ），１．７５−１．６２（２Ｈ，ｍ），１．０８−１．００（９Ｈ，ｍ） <Production of Compound represented by Formula 1-74>

At room temperature, 810 mg of 28% sodium methoxide methanol solution and 560 mg of the compound represented by the formula (8-1) were dissolved in 15 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 1.1 g of the compound represented by the formula (7-17) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The obtained reaction liquid was cooled to room temperature, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane in order to obtain 1.6 g of a compound represented by the formula (6-17).
Subsequently, 1.6 g of the compound represented by the formula (6-17) was dissolved in 30 ml of water at room temperature. To the resulting solution was added 1.2 g of anhydrous sodium carbonate. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, acidified with 2N hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 1.2 g of a compound represented by the formula (2-17).
Subsequently, 600 mg of the compound represented by the formula (2-17) and 1.05 g of dimethylamipyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene at room temperature under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 5) to obtain 200 mg of a compound represented by the formula (1-74).
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, s), 7.66 (1H, dd), 7.27 (1H, d), 6.98 (2H, s), 5.52 (1H, s), 3. 57-3.46 (1H, m), 3.31-3.17 (1H, m), 2.71-2.58 (3H, m), 2.44-2.25 (10H, m), 1.75-1.62 (2H, m), 1.08-1.00 (9H, m)

室温にて式（１１−１）で示される化合物３１ｇ、ピリジン１７ｍｌおよび塩化メチレン１００ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、パラトルエンスルホニルクロライド１１．４ｇを塩化メチレン６０ｍｌに溶解して得られた混合液へ滴下した。得られた混合液を０℃氷冷下、３時間攪拌した。得られた反応混合液を酢酸エチルで希釈して、飽和炭酸水素ナトリウム水溶液で洗浄した。得られた酢酸エチル層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した後、濾過した。得られたろ液を減圧濃縮して油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィー(溶出液、酢酸エチル：ヘキサン＝３：２)に付し、式（１２−１）で示される化合物１６ｇ(無色油状物質)を得た。
１Ｈ ＮＭＲ （ＣＤＣｌ₃）
δ ｐｐｍ ：７．８０−７．７８（２Ｈ，ｍ），７．３４−７．３０（２Ｈ，ｍ），３．８２（２Ｈ，ｓ），３．３７（２Ｈ，ｓ），２．４５（３Ｈ，ｓ），０．８８（６Ｈ，ｓ） Production Example 1-23: Production of compound represented by formula (1-21) <Production of compound represented by formula 12-1>

31 g of the compound represented by the formula (11-1), 17 ml of pyridine and 100 ml of methylene chloride were mixed and stirred at room temperature. The resulting mixture was cooled to 0 ° C. It was dripped at the liquid mixture obtained by melt | dissolving in. The resulting mixture was stirred for 3 hours under ice cooling at 0 ° C. The resulting reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate. The obtained ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 3: 2) to obtain 16 g (colorless oily substance) of the compound represented by the formula (12-1).
1H NMR (CDCl ₃ )
δ ppm: 7.80-7.78 (2H, m), 7.34-7.30 (2H, m), 3.82 (2H, s), 3.37 (2H, s), 2.45 (3H, s), 0.88 (6H, s)

窒素雰囲気下、６０％水素化ナトリウム１．５５ｇに無水Ｎ，Ｎ−ジメチルホルムアミド３０ｍｌを添加した。得られた混合物に氷冷下、式（１０−１）で示される化合物７．２ｇを滴下した。得られた混合物を氷冷下２５分間攪拌した後、そこに式（１２−１）で示される化合物８ｇの無水ＤＭＦ１５ｍｌ溶液を滴下し、得られた混合物を室温下１時間攪拌した後、反応温度を９０℃まで昇温し８時間攪拌した。得られた反応混合液をt−ブチルメチルエーテルで抽出した。有機層を合し、水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧濃縮し、粗生成物を得た。この粗製生物をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４→２：３）に付し、式（１３−１）で示される化合物７．６ｇを得た（油状物質）。
１Ｈ ＮＭＲ （ＣＤＣｌ₃）
δ ｐｐｍ ：７．４８（２Ｈ，ｄ），７．３９（２Ｈ，ｄ），３．４５（２Ｈ，ｓ），３．０２（２Ｈ，ｓ），２．０３(１Ｈ，ｓ), １．０１（６Ｈ，ｓ） <Production of Compound represented by Formula 13-1>

Under a nitrogen atmosphere, 30 ml of anhydrous N, N-dimethylformamide was added to 1.55 g of 60% sodium hydride. To the obtained mixture, 7.2 g of the compound represented by the formula (10-1) was added dropwise under ice cooling. The obtained mixture was stirred for 25 minutes under ice-cooling, and then a solution of 8 g of the compound represented by the formula (12-1) in 15 ml of anhydrous DMF was added dropwise. The resulting mixture was stirred at room temperature for 1 hour, and then the reaction temperature Was heated to 90 ° C. and stirred for 8 hours. The resulting reaction mixture was extracted with t-butyl methyl ether. The organic layers were combined, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product. This crude product was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4 → 2: 3) to obtain 7.6 g of a compound represented by the formula (13-1) (oily substance).
1H NMR (CDCl ₃ )
δ ppm: 7.48 (2H, d), 7.39 (2H, d), 3.45 (2H, s), 3.02 (2H, s), 2.03 (1H, s), 01 (6H, s)

窒素雰囲気下、塩化オキサリル３．４ｍｌと塩化メチレン１２０mlの混合液をー７８℃まで冷却した後、ジメチルスルホキシド５．７ｍｌをゆっくりと滴下し、１０分間攪拌した。その後、得られた混合液に式（１３−１）で示される化合物７．６ｇの塩化メチレン５０ｍｌ溶液を滴下し、３０分間攪拌した。その後、得られた混合液にトリエチルアミン１１．６ｇを加え、−７８℃で１時間攪拌した後、０℃氷冷下でさらに６時間攪拌した。得られた反応液をクロロホルムで希釈して、１Ｎ水酸化ナトリウム水溶液で洗浄した。得られたクロロホルム層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した後、濾過した。得られたろ液を減圧濃縮して式（９−１８）で示される化合物６．７ｇ(油状物質)を得た。
１Ｈ ＮＭＲ （ＣＤＣｌ₃）
δ ｐｐｍ ：９．５０（１Ｈ，ｓ），７．５１（２Ｈ，ｄ），７．４０（２Ｈ，ｄ），３．１６（２Ｈ，ｓ），１．２４（６Ｈ，ｓ） <Production of compound represented by formula 9-18>

Under a nitrogen atmosphere, a mixture of 3.4 ml of oxalyl chloride and 120 ml of methylene chloride was cooled to −78 ° C., and then 5.7 ml of dimethyl sulfoxide was slowly added dropwise and stirred for 10 minutes. Thereafter, a solution of 7.6 g of the compound represented by the formula (13-1) in 50 ml of methylene chloride was added dropwise to the obtained mixed solution, followed by stirring for 30 minutes. Thereafter, 11.6 g of triethylamine was added to the obtained mixture, and the mixture was stirred at -78 ° C for 1 hour, and further stirred at 0 ° C under ice cooling for 6 hours. The resulting reaction solution was diluted with chloroform and washed with 1N aqueous sodium hydroxide solution. The obtained chloroform layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain 6.7 g (oily substance) of the compound represented by the formula (9-18).
1H NMR (CDCl ₃ )
δ ppm: 9.50 (1H, s), 7.51 (2H, d), 7.40 (2H, d), 3.16 (2H, s), 1.24 (6H, s)

室温にて、式（９−１８）で示される化合物４．２ｇおよびトリフェニルホスフィンアセチルメチレン５．６ｇをキシレン２０ｍｌに溶解した。得られた溶液を８時間加熱還流した。その後、減圧下、得られた反応液からキシレンを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−１８）で示される化合物４．１ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５０（２Ｈ，ｄ），７．３８（２Ｈ，ｄ），６．７３（１Ｈ，ｄｄ），６．０５（１Ｈ，ｄｄ），３．０６（２Ｈ，ｓ），２．１７（３Ｈ，ｓ），１．２３（６Ｈ，ｓ） <Production of Compound represented by Formula 7-18>

At room temperature, 4.2 g of the compound represented by the formula (9-18) and 5.6 g of triphenylphosphine acetylmethylene were dissolved in 20 ml of xylene. The resulting solution was heated to reflux for 8 hours. Thereafter, xylene was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 4.1 g of a compound represented by the formula (7-18).
1H NMR (CDCl ₃ )
δ ppm: 7.50 (2H, d), 7.38 (2H, d), 6.73 (1H, dd), 6.05 (1H, dd), 3.06 (2H, s), 2. 17 (3H, s), 1.23 (6H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液２．９ｇおよび式（８−１）で示される化合物２．０ｇを１，４−ジオキサン３５ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−１８）で示される化合物４．１ｇを加えた。その後、得られた混合液を１時間加熱還流した。得られた反応液を室温まで冷却し、減圧濃縮し、析出した粗結晶をｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−１８）で示される化合物５．７ｇを得た。
引き続き、室温にて、式（６−１８）で示される化合物５．７ｇを水２５ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム１．０５ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−１８）で示される化合物９７０mｇを得た。
続いて、窒素雰囲気下、室温にて、式（２−１８）で示される化合物９７０ｍｇおよびジメチルアミピリジン１．７ｇをクロロホルム７．５ｍｌとトルエン２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．５ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−２１）で示される化合物３００ｍｇ（白色固体）を得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５２（２Ｈ，ｄ），７．４１（２Ｈ，ｄ），６．９９（２Ｈ，ｓ），５．５４（１Ｈ，ｓ），３．０４（２Ｈ，ｄｄ），２．６７−２．２４（１２Ｈ，ｍ），１．１３−１．０６（１２Ｈ，ｍ） <Production of compound represented by formula 1-21>

At room temperature, 2.9 g of 28% sodium methoxide methanol solution and 2.0 g of the compound represented by the formula (8-1) were dissolved in 35 ml of 1,4-dioxane. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 4.1 g of the compound represented by the formula (7-18) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 1 hour. The resulting reaction solution was cooled to room temperature, concentrated under reduced pressure, and the precipitated crude crystals were washed well with tert-butyl methyl ether and hexane in order to obtain 5.7 g of a compound represented by the formula (6-18). .
Subsequently, 5.7 g of the compound represented by the formula (6-18) was dissolved in 25 ml of water at room temperature. 1.05 g of anhydrous sodium carbonate was added to the resulting solution. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 970 mg of a compound represented by the formula (2-18).
Subsequently, 970 mg of the compound represented by the formula (2-18) and 1.7 g of dimethylamipyridine were dissolved in a mixture of 7.5 ml of chloroform and 2 ml of toluene at room temperature under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.5 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 300 mg (white solid) of the compound represented by the formula (1-21).
1H NMR (CDCl ₃ )
δ ppm: 7.52 (2H, d), 7.41 (2H, d), 6.99 (2H, s), 5.54 (1H, s), 3.04 (2H, dd), 2. 67-2.24 (12H, m), 1.13-1.06 (12H, m)

窒素雰囲気下、６０％水素化ナトリウム１．５５ｇに無水Ｎ，Ｎ−ジメチルホルムアミド３０ｍｌを添加した。得られた混合物に氷冷下、式（１０−２）で示される化合物７．２ｇを滴下した。得られた混合物を氷冷下２５分間攪拌した後、そこに式（１２−１）で示される化合物８ｇの無水Ｎ，Ｎ−ジメチルホルムアミド１５ｍｌ溶液を滴下し、得られた混合物を室温下１時間攪拌した後、反応温度を９０℃まで昇温し８時間攪拌した。得られた反応混合液をtert−ブチルメチルエーテルで抽出した。有機層を合し、水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧濃縮し、粗生成物を得た。この粗製生物をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１３−２）で示される化合物６．７ｇを得た。
１Ｈ ＮＭＲ （ＣＤＣｌ₃）
δ ｐｐｍ ：８．６１(１Ｈ，ｓ)，７．７０−７．６７（１Ｈ，ｍ），７．３６−７．３２（２Ｈ，ｍ），３．３０（２Ｈ，ｄ），３．２３（２Ｈ，ｄ），１．０４（６Ｈ，ｓ） Production Example 1-24: Production of compound represented by formula (1-22) <Production of compound represented by formula 13-2>

Under a nitrogen atmosphere, 30 ml of anhydrous N, N-dimethylformamide was added to 1.55 g of 60% sodium hydride. To the obtained mixture, 7.2 g of the compound represented by the formula (10-2) was added dropwise under ice cooling. The obtained mixture was stirred for 25 minutes under ice-cooling, and then a solution of 8 g of the compound represented by formula (12-1) in 15 ml of anhydrous N, N-dimethylformamide was added dropwise, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, the reaction temperature was raised to 90 ° C. and stirred for 8 hours. The resulting reaction mixture was extracted with tert-butyl methyl ether. The organic layers were combined, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product. This crude product was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 6.7 g of a compound represented by the formula (13-2).
1H NMR (CDCl ₃ )
δ ppm: 8.61 (1H, s), 7.70-7.67 (1H, m), 7.36-7.32 (2H, m), 3.30 (2H, d), 3.23 (2H, d), 1.04 (6H, s)

窒素雰囲気下、塩化オキサリル３．１ｍｌと塩化メチレン１２０mlの混合液を−７８℃まで冷却した後、ジメチルスルホキシド５．０ｍｌをゆっくりと滴下し、１０分間攪拌した。その後、得られた混合液に式（１３−２）で示される化合物６．７ｇの塩化メチレン５０ｍｌ溶液を滴下し、３０分間攪拌した。その後、得られた混合液にトリエチルアミン１０．３ｇを加え、−７８℃で１時間攪拌した後、０℃氷冷下で６時間攪拌した。得られた反応液をクロロホルムで希釈して、１Ｎ水酸化ナトリウム水溶液で洗浄した。得られたクロロホルム層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した後、濾過した。得られたろ液を減圧濃縮して式（９−１９）で示される化合物６．２ｇを得た。
１Ｈ ＮＭＲ （ＣＤＣｌ₃）
δ ｐｐｍ ：９．５１（１Ｈ，ｓ），８．６４(１Ｈ，ｓ），７．６５（１Ｈ，ｄ），７．２７（１Ｈ，ｄ），３．５２（２Ｈ，ｓ），１．２４（６Ｈ，ｓ） <Production of compound represented by formula 9-19>

Under a nitrogen atmosphere, a mixed solution of 3.1 ml of oxalyl chloride and 120 ml of methylene chloride was cooled to −78 ° C., 5.0 ml of dimethyl sulfoxide was slowly added dropwise and stirred for 10 minutes. Thereafter, a solution of 6.7 g of the compound represented by the formula (13-2) in 50 ml of methylene chloride was added dropwise to the obtained mixed solution, and the mixture was stirred for 30 minutes. Thereafter, 10.3 g of triethylamine was added to the obtained mixture, and the mixture was stirred at -78 ° C for 1 hour, and then stirred at 0 ° C under ice cooling for 6 hours. The resulting reaction solution was diluted with chloroform and washed with 1N aqueous sodium hydroxide solution. The obtained chloroform layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain 6.2 g of a compound represented by the formula (9-19).
1H NMR (CDCl ₃ )
δ ppm: 9.51 (1H, s), 8.64 (1H, s), 7.65 (1H, d), 7.27 (1H, d), 3.52 (2H, s), 1. 24 (6H, s)

室温にて、式（９−１９）で示される化合物４．６ｇおよびトリフェニルホスフィンアセチルメチレン６．２ｇをキシレン２５ｍｌに溶解した。得られた溶液を８時間加熱還流した。その後、得られた反応液を減圧下、キシレンを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。続いて、得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−１９）で示される化合物３．８ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６４（１Ｈ，ｓ），７．６４（１Ｈ，ｄｄ），７．２７(１Ｈ，ｄ），６．０４（１Ｈ，ｄ），６．０４（１Ｈ，ｄ），３．４３（２Ｈ，ｓ），２．１７（３Ｈ，ｓ），１．２２（６Ｈ，ｓ） <Production of Compound represented by Formula 7-19>

At room temperature, 4.6 g of the compound represented by the formula (9-19) and 6.2 g of triphenylphosphine acetylmethylene were dissolved in 25 ml of xylene. The resulting solution was heated to reflux for 8 hours. Thereafter, xylene was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. Subsequently, the obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 3.8 g of a compound represented by the formula (7-19).
1H NMR (CDCl ₃ )
δ ppm: 8.64 (1H, s), 7.64 (1H, dd), 7.27 (1H, d), 6.04 (1H, d), 6.04 (1H, d), 3. 43 (2H, s), 2.17 (3H, s), 1.22 (6H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液２．７ｇおよび式（８−１）で示される化合物１．８ｇを１，４−ジオキサン３５ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−１９）で示される化合物３．８ｇを加えた。その後、得られた混合液を１時間加熱還流した。得られた反応液を室温まで冷却し、減圧濃縮し、析出した粗結晶をｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次よく洗浄し、式（６−１９）で示される化合物５．３ｇを得た。
引き続き、室温にて、式（６−１９）で示される化合物５．３ｇを水９５ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム４．０ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄して不純物を除去した後、２Ｎ塩酸を加えて酸性にした水層を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−１９）で示される化合物２．８ｇを得た。
続いて、窒素雰囲気下、室温にて、式（２−１９）で示される化合物６００ｍｇおよびジメチルアミピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．０ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：５）に付し、式（１−２２）で示される化合物２９０ｍｇ（白色固体）を得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６５(１Ｈ，ｓ），７．６５（１Ｈ，ｄｄ），７．３０（１Ｈ，ｄ），６．９８（２Ｈ，ｓ），５．５４（１Ｈ，ｓ），３．４１（２Ｈ，ｄｄ），２．７８−２．５１（３Ｈ，ｍ），２．４８−２．２６（９Ｈ，ｍ），１．１８−１．００（１２Ｈ，ｍ） <Production of Compound represented by Formula 1-22>

At room temperature, 2.7 g of 28% sodium methoxide methanol solution and 1.8 g of the compound represented by the formula (8-1) were dissolved in 35 ml of 1,4-dioxane. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 3.8 g of the compound represented by the formula (7-19) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 1 hour. The obtained reaction liquid was cooled to room temperature, concentrated under reduced pressure, and the precipitated crude crystals were washed well with tert-butyl methyl ether and hexane in order to obtain 5.3 g of a compound represented by the formula (6-19). .
Subsequently, 5.3 g of the compound represented by the formula (6-19) was dissolved in 95 ml of water at room temperature. To the resulting solution was added anhydrous sodium carbonate 4.0 g. The resulting solution was heated to reflux for 5 hours. The reaction solution was cooled to room temperature, washed with tert-butyl methyl ether to remove impurities, and then the aqueous layer made acidic by adding 2N hydrochloric acid was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 2.8 g of a compound represented by the formula (2-19).
Subsequently, 600 mg of the compound represented by the formula (2-19) and 1.05 g of dimethylamipyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene at room temperature under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.0 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 5) to obtain 290 mg (white solid) of the compound represented by the formula (1-22).
1H NMR (CDCl ₃ )
δ ppm: 8.65 (1H, s), 7.65 (1H, dd), 7.30 (1H, d), 6.98 (2H, s), 5.54 (1H, s), 3. 41 (2H, dd), 2.78-2.51 (3H, m), 2.48-2.26 (9H, m), 1.18-1.00 (12H, m)

窒素雰囲気下、室温にて、四酢酸鉛１０ｇ、酢酸水銀３１０ｍｇおよび式（５−３）で示される化合物５ｇをクロロホルム４０ｍｌに溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、反応液を４０℃で４時間攪拌した。反応液を室温まで冷却し、セライト（登録商標）濾過した。得られたろ液を減圧濃縮して赤色油状物質を得た。得られた油状物質にヘキサンを加え、得られたものを減圧濃縮して式(３−３)で示される化合物１０．２ｇ（赤色固体）を得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．６１−７．５９（１Ｈ， ｍ）、７．４１−７．３４（５Ｈ，ｍ），７．００−６．９７（２Ｈ，ｍ）、５．０８（２Ｈ，ｓ）、２．８３（２Ｈ，ｑ）、２．０９（９Ｈ，ｓ），１．２９（３Ｈ，ｔ） Production Example 1-25: Production of compound represented by formula (1-40) <Production of compound represented by formula 3-3>

Under a nitrogen atmosphere, at room temperature, 10 g of lead tetraacetate, 310 mg of mercury acetate and 5 g of the compound represented by the formula (5-3) were dissolved in 40 ml of chloroform. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, the reaction solution was stirred at 40 ° C. for 4 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature and filtered through Celite (registered trademark). The obtained filtrate was concentrated under reduced pressure to obtain a red oily substance. Hexane was added to the obtained oily substance, and the obtained substance was concentrated under reduced pressure to obtain 10.2 g (red solid) of the compound represented by the formula (3-3).
1H NMR (CDCl ₃ )
δ ppm: 7.61-7.59 (1H, m), 7.41-7.34 (5H, m), 7.00-6.97 (2H, m), 5.08 (2H, s) 2.83 (2H, q), 2.09 (9H, s), 1.29 (3H, t)

窒素雰囲気下、室温にて、式（２−２）で示される化合物５４０ｍｇおよびジメチルアミノピリジン１．０５ｇをクロロホルム４．８ｍｌとトルエン１．２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−３）で示される化合物１．１ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：２）に付し、式（３４−１）で示される化合物３８６ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６７（１Ｈ，ｓ），７．６７（１Ｈ，ｄｄ），７．４６−７．２６（６Ｈ，ｍ），６．９８−６．９２(２Ｈ，ｍ)，６．８６(１Ｈ，ｄｔ)，５．７４（１Ｈ，ｓ），５．０８(２Ｈ，ｓ)，３．３０（２Ｈ，ｔ），２．７９−２．６７（２Ｈ，ｍ），２．５０−２．２４（５Ｈ，ｍ），１．９３−１．８７（２Ｈ，ｍ），１．０８（３Ｈ，ｄｔ） <Production of Compound represented by Formula 34-1>

Under a nitrogen atmosphere, at room temperature, 540 mg of the compound represented by the formula (2-2) and 1.05 g of dimethylaminopyridine were dissolved in a mixture of 4.8 ml of chloroform and 1.2 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.1 g of the compound represented by the formula (3-3) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 2) to obtain 386 mg of a compound represented by the formula (34-1).
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, s), 7.67 (1H, dd), 7.46-7.26 (6H, m), 6.98-6.92 (2H, m), 6.86 (1H, dt), 5.74 (1H, s), 5.08 (2H, s), 3.30 (2H, t), 2.79-2.67 (2H, m), 2.50- 2.24 (5H, m), 1.93-1.87 (2H, m), 1.08 (3H, dt)

室温下、式（３４−１）で示される化合物３００ｍｇを酢酸２．２mlに溶解し、得られた混合液に４７％臭化水素酸０．７ｍｌを滴下した。得られた反応液を１００℃まで加熱し、３０分間攪拌した。反応液に氷水１０ｍｌを加え、酢酸エチルで抽出した。得られた酢酸エチル層を水で洗浄し、無水硫酸ナトリウムで乾燥した後、濾過した。得られたろ液を減圧濃縮し、式（３５−１）で示される化合物２４０ｍｇを得た。
引き続いて、室温にて式（３５−１）で示される化合物２４０ｍｇ、炭酸セシウム２００ｍｇと２，３−ジクロロー5−トリフルオロメチルピリジン１１８ｍｇをＮ，Ｎ−ジメチルホルムアミド２mlに溶解した。得られた反応液を７０℃まで加熱して、２時間攪拌した。得られた反応液を酢酸エチルで抽出し、得られた酢酸エチル層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した後、濾過した。得られたろ液を減圧濃縮後、シリカゲルカラムクロマトグラフィー（溶出液、酢酸エチル：ヘキサン＝１：２）に付し、式（１−４０）で示される化合物８０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６８（１Ｈ，ｓ），８．２４（１Ｈ，ｄｄ），８．００（１Ｈ，ｄ），７．６７（１Ｈ，ｄｄ），７．２８−７．２６(１Ｈ，ｍ)，７．１４−７．０３（３Ｈ，ｍ）、６．３３(１Ｈ，ｓ)，３．３１（２Ｈ，ｔ），２．７９−２．６８（２Ｈ，ｍ），２．５２−２．２６（５Ｈ，ｍ），１．９４−１．８９（２Ｈ，ｍ），１．１０（３Ｈ，ｄｔ）
<Production of Compound represented by Formula 1-40>

At room temperature, 300 mg of the compound represented by formula (34-1) was dissolved in 2.2 ml of acetic acid, and 0.7 ml of 47% hydrobromic acid was added dropwise to the resulting mixture. The resulting reaction solution was heated to 100 ° C. and stirred for 30 minutes. To the reaction solution was added 10 ml of ice water, and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate, and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain 240 mg of the compound represented by the formula (35-1).
Subsequently, 240 mg of the compound represented by the formula (35-1), 200 mg of cesium carbonate and 118 mg of 2,3-dichloro-5-trifluoromethylpyridine were dissolved in 2 ml of N, N-dimethylformamide at room temperature. The resulting reaction solution was heated to 70 ° C. and stirred for 2 hours. The resulting reaction solution was extracted with ethyl acetate, and the resulting ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then filtered. The obtained filtrate was concentrated under reduced pressure, and then subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 2) to obtain 80 mg of a compound represented by the formula (1-40).
1H NMR (CDCl ₃ )
δ ppm: 8.68 (1H, s), 8.24 (1H, dd), 8.00 (1H, d), 7.67 (1H, dd), 7.28-7.26 (1H, m ), 7.14-7.03 (3H, m), 6.33 (1H, s), 3.31 (2H, t), 2.79-2.68 (2H, m), 2.52- 2.26 (5H, m), 1.94-1.89 (2H, m), 1.10 (3H, dt)

室温にて、式（７−２０）で示される化合物１０ｇを酢酸３３ｍｌに溶解した。得られた混合液に３５％硫酸１００ｍｌを加えた。その後、得られた反応混合液を０℃まで冷却した後、亜硝酸ナトリウム３．３ｇと水２５ｍｌとの混合物を滴下し、０℃にて１０分間攪拌した。
その後、得られた反応液を、硫化ナトリウム１５ｇと硫黄２ｇと水酸化ナトリウム３．３ｇとを６０℃にて水１００ｍｌに溶解した混合物に滴下し、３０分間攪拌した。反応液を室温まで冷却した後、ｔｅｒｔ−ブチルメチルエーテルで抽出、１０％塩酸水で洗浄後、無水硫酸ナトリウムで乾燥した後、濾過した。得られたろ液を減圧乾燥し、ジエチルエーテル３００ｍｌに溶解し、窒素雰囲気下、０℃にてリチウムアルミニウムハイドライド１．８ｇを加え、その後、室温下、１時間攪拌した。得られた反応混合液へ１０％塩酸水を５００ｍｌ加え、ジエチルエーテルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した後、濾過した。得られたろ液を減圧濃縮して、式（１０−１７）で示される化合物の粗生成物を得た。得られた粗生成物をシリカゲルカラムクロマトグラフィー（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１０−１７）で示される化合物３．１ｇを得た。
その後、室温にて、式（１０−１７）で示される化合物３．０ｇおよびテトラヒドロフラン１０ｍｌを混合、攪拌し、得られた混合物を０℃まで冷却した後、そこにアクロレイン１．０５ｇとトリエチルアミン０．１ｇを滴下した。得られた混合物を氷冷下２時間攪拌した。その後、得られた混合物に水を加え、ｔｅｒｔ−ブチルメチルエーテルにて抽出した。有機層を水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧濃縮して、式（９−２０）で示される化合物１．２ｇを得た。
引き続き、室温にて、式（９−２０）で示される化合物１．２ｇおよびトリフェニルホスフィンアセチルメチレン１．４ｇをクロロホルム５ｍｌに溶解した。得られた溶液を０℃で、８時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−２０）で示される化合物３４０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．６６(２Ｈ，ｄ)，７．３２(２Ｈ，ｄ)，６．７８（１Ｈ，ｄｔ），６．１４（１Ｈ，ｄ），３．１２（２Ｈ，ｔ），２．６１（２Ｈ，ｑ），２．２５（３Ｈ，ｓ） Production Example 1-26: Production of compound represented by formula (1-75) <Production of compound represented by formula 7-20>

At room temperature, 10 g of the compound represented by the formula (7-20) was dissolved in 33 ml of acetic acid. 100 ml of 35% sulfuric acid was added to the resulting mixture. Then, after cooling the obtained reaction liquid mixture to 0 degreeC, the mixture of 3.3 g of sodium nitrite and 25 ml of water was dripped, and it stirred at 0 degreeC for 10 minutes.
Thereafter, the obtained reaction solution was added dropwise to a mixture of 15 g of sodium sulfide, 2 g of sulfur, and 3.3 g of sodium hydroxide dissolved in 100 ml of water at 60 ° C., and stirred for 30 minutes. The reaction solution was cooled to room temperature, extracted with tert-butyl methyl ether, washed with 10% aqueous hydrochloric acid, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was dried under reduced pressure, dissolved in 300 ml of diethyl ether, added with 1.8 g of lithium aluminum hydride at 0 ° C. in a nitrogen atmosphere, and then stirred at room temperature for 1 hour. To the resulting reaction mixture, 500 ml of 10% aqueous hydrochloric acid was added and extracted with diethyl ether. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain a crude product of the compound represented by the formula (10-17). The obtained crude product was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 3.1 g of a compound represented by the formula (10-17).
Thereafter, at room temperature, 3.0 g of the compound represented by the formula (10-17) and 10 ml of tetrahydrofuran were mixed and stirred, and the resulting mixture was cooled to 0 ° C. Then, 1.05 g of acrolein and 0. 1 g was added dropwise. The resulting mixture was stirred for 2 hours under ice cooling. Then, water was added to the obtained mixture and extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 1.2 g of a compound represented by the formula (9-20).
Subsequently, 1.2 g of the compound represented by the formula (9-20) and 1.4 g of triphenylphosphine acetylmethylene were dissolved in 5 ml of chloroform at room temperature. The resulting solution was stirred at 0 ° C. for 8 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 340 mg of a compound represented by the formula (7-20).
1H NMR (CDCl ₃ )
δ ppm: 7.66 (2H, d), 7.32 (2H, d), 6.78 (1H, dt), 6.14 (1H, d), 3.12 (2H, t), 2. 61 (2H, q), 2.25 (3H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液２２０ｇおよび式（８−１）で示される化合物１５０ｍｇをテトラヒドロフラン４ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−２０）で示される化合物３４０ｍｇを加えた。その後、得られた混合液を３０分間加熱還流した。得られた反応液を０℃まで冷却し、ヘキサンを加え、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次洗浄し、式（６−２０）で示される化合物４６０ｍｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：７．８０（２Ｈ，ｄ），７．４４（２Ｈ，ｄ），４．３９（１Ｈ，ｓ），３．６５−３．４８（４Ｈ，ｍ），３．１７−３．１０（１Ｈ，ｍ），２．９９−２．９１（１Ｈ，ｍ），２．８３（１Ｈ，ｄ），２．３２−２．２５（１Ｈ，ｍ），２．１５−２．０３（１Ｈ，ｍ），１．８５−１．７４（１Ｈ，ｍ），１．５３−１．４７（１Ｈ，ｍ） <Production of Compound represented by Formula 6-20>

At room temperature, 28 g of a 28% sodium methoxide methanol solution and 150 mg of the compound represented by the formula (8-1) were dissolved in 4 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 340 mg of the compound represented by the formula (7-20) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 30 minutes. The obtained reaction solution was cooled to 0 ° C., hexane was added, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane to obtain 460 mg of the compound represented by the formula (6-20). It was.
1H NMR (d-DMSO)
δ ppm: 7.80 (2H, d), 7.44 (2H, d), 4.39 (1H, s), 3.65-3.48 (4H, m), 3.17-3.10 (1H, m), 2.99-2.91 (1H, m), 2.83 (1H, d), 2.32-2.25 (1H, m), 2.15-2.03 (1H , M), 1.85-1.74 (1H, m), 1.53-1.47 (1H, m)

室温にて、式（６−２０）で示される化合物４６０ｍｇを水１０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム３２３ｍｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄した後、水層に２Ｎ塩酸を加えて酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−２０）で示される化合物４００ｍｇを得た。
続いて、窒素雰囲気下、室温にて、式（２−２０）で示される化合物４００ｍｇおよびジメチルアミピリジン６２０ｍｇをクロロホルム３ｍｌとトルエン１ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物６００ｍｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１−７５）で示される化合物１５０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．６６（２Ｈ，ｄ），７．３２（２Ｈ，ｄ），６．９８（２Ｈ，ｓ），５．５７（１Ｈ，ｓ），３．１３−３．０１（２Ｈ，ｍ），２．７７−２．６８（２Ｈ，ｍ），２．４９−２．２２（１０Ｈ，ｍ），１．８８（２Ｈ，ｑ），１．０６（６Ｈ，ｄｄｄ） <Production of Compound represented by Formula 1-75>

At room temperature, 460 mg of the compound represented by the formula (6-20) was dissolved in 10 ml of water. To the resulting solution was added anhydrous sodium carbonate 323 mg. The resulting solution was heated to reflux for 5 hours. The reaction mixture was cooled to room temperature, washed with tert-butyl methyl ether, 2N hydrochloric acid was added to the aqueous layer, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 400 mg of the compound represented by the formula (2-20).
Subsequently, 400 mg of the compound represented by the formula (2-20) and 620 mg of dimethylamipyridine were dissolved in a mixture of 3 ml of chloroform and 1 ml of toluene at room temperature under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 600 mg of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 150 mg of a compound represented by the formula (1-75).
1H NMR (CDCl ₃ )
δ ppm: 7.66 (2H, d), 7.32 (2H, d), 6.98 (2H, s), 5.57 (1H, s), 3.13-3.01 (2H, m ), 2.77-2.68 (2H, m), 2.49-2.22 (10H, m), 1.88 (2H, q), 1.06 (6H, ddd)

室温にて式（１０−１）で示される化合物１０ｇをジメチルホルムアミド５０ｍｌに溶解した。得られた混合液に室温にてトリエチルアミン５．７ｇを加え、超音波をかけながら６時間攪拌した。得られた反応混合液をｔｅｒｔ−メチルエチルエーテルで抽出し、得られた有機層を水で洗浄し、無水硫酸ナトリウムで乾燥した後、濾過した。得られたろ液を減圧濃縮し、式（２１−１）で示される化合物９．３ｇを得た。（無色固体）
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．６０−７．５３（８H, ｍ） Production Example 1-27: Production of compound represented by formula (1-23) <Production of compound represented by formula 21-1>

At room temperature, 10 g of the compound represented by the formula (10-1) was dissolved in 50 ml of dimethylformamide. To the obtained mixture, 5.7 g of triethylamine was added at room temperature, and the mixture was stirred for 6 hours while applying ultrasonic waves. The resulting reaction mixture was extracted with tert-methyl ethyl ether, and the resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain 9.3 g of a compound represented by the formula (21-1). (Colorless solid)
1H NMR (CDCl ₃ )
δ ppm: 7.60-7.53 (8H, m)

式（１１−２）で示される化合物５ｇと式（２１−１）で示される化合物９．３ｇとをテトラヒドロフラン２５０ｍｌに溶解した。窒素雰囲気下、室温にて、得られた混合液にトリブチルホスフィン５．８ｇを滴下し、２時間攪拌した。得られた反応混合液を減圧濃縮し、得られた粗生成物をシリカゲルカラムクロマトグラフィー（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１３−３）で示される化合物４．５ｇを得た。(無色固体)
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５０（２Ｈ，ｄ）、７．４１（２Ｈ，ｄ）、３．５８（２Ｈ，ｓ），３．１７（２Ｈ，ｓ），０．５８（４Ｈ，ｓ） <Production of compound represented by formula 13-3>

5 g of the compound represented by the formula (11-2) and 9.3 g of the compound represented by the formula (21-1) were dissolved in 250 ml of tetrahydrofuran. In a nitrogen atmosphere at room temperature, 5.8 g of tributylphosphine was added dropwise to the obtained mixed solution and stirred for 2 hours. The obtained reaction mixture was concentrated under reduced pressure, and the resulting crude product was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to give compound 4 represented by formula (13-3). .5 g was obtained. (Colorless solid)
1H NMR (CDCl ₃ )
δ ppm: 7.50 (2H, d), 7.41 (2H, d), 3.58 (2H, s), 3.17 (2H, s), 0.58 (4H, s)

窒素雰囲気下、塩化オキサリル２．５ｇと塩化メチレン４５mlとの混合液を−７８℃まで冷却した後、ジメチルスルホキシド２．７ｇの塩化メチレン２０ｍｌ溶液を滴下し、１０分間攪拌した。その後、得られた混合液に式（１３−３）で示される化合物４．５ｇの塩化メチレン５ｍｌ溶液を滴下し、３０分間攪拌した。その後、得られた混合液にトリエチルアミン８．８ｇを加え、室温まで昇温し、３時間攪拌した。得られた反応液を１Ｎ塩酸水６０ｍｌに注ぎ、クロロホルムで抽出した。得られた有機層を無水硫酸ナトリウムで乾燥した後、濾過した。得られたろ液を減圧濃縮して式（９−２１）で示される化合物の粗生成物４．５ｇを得た。
引き続き、室温にて、式（９−２１）で示される化合物の粗生成物４．５ｇおよびトリフェニルホスフィンアセチルメチレン６．１ｇをキシレン４５ｍｌに溶解した。得られた反応混合溶液を８時間加熱還流した。その後、得られた反応液を減圧下、キシレンを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。続いて、得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−２１）で示される化合物３．８ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５２（２Ｈ，ｄ），７．３５（２Ｈ，ｄ），６．４９（１Ｈ，ｄ），６．１７（１Ｈ，ｄ），３．１９（２Ｈ，ｓ），２．２２（３Ｈ，ｓ），１．１０−１．００（４Ｈ，ｍ） <Production of Compound represented by Formula 7-21>

Under a nitrogen atmosphere, a mixed solution of 2.5 g of oxalyl chloride and 45 ml of methylene chloride was cooled to −78 ° C., and then a solution of 2.7 g of dimethyl sulfoxide in 20 ml of methylene chloride was added dropwise and stirred for 10 minutes. Thereafter, a solution of 4.5 g of the compound represented by the formula (13-3) in 5 ml of methylene chloride was added dropwise to the obtained mixed solution, followed by stirring for 30 minutes. Thereafter, 8.8 g of triethylamine was added to the obtained mixture, and the mixture was warmed to room temperature and stirred for 3 hours. The resulting reaction solution was poured into 60 ml of 1N aqueous hydrochloric acid and extracted with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain 4.5 g of a crude product of the compound represented by the formula (9-21).
Subsequently, 4.5 g of a crude product of the compound represented by the formula (9-21) and 6.1 g of triphenylphosphine acetylmethylene were dissolved in 45 ml of xylene at room temperature. The resulting reaction mixture was heated to reflux for 8 hours. Thereafter, xylene was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. Subsequently, the obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 3.8 g of a compound represented by the formula (7-21).
1H NMR (CDCl ₃ )
δ ppm: 7.52 (2H, d), 7.35 (2H, d), 6.49 (1H, d), 6.17 (1H, d), 3.19 (2H, s), 2. 22 (3H, s), 1.10-1.00 (4H, m)

室温にて、２８％ナトリウムメトキシドメタノール溶液２．７ｇおよび式（８−１）で示される化合物１．８ｇを１，４−ジオキサン３０ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−２１）で示される化合物３．８ｇを加えた。その後、得られた混合液を１時間加熱還流した。得られた反応液を０℃まで冷却し、ヘキサンを加え、析出した結晶をろ過して、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次洗浄し、式（６−２１）で示される化合物４．５ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．６２（２Ｈ，ｄ），７．４５（２Ｈ，ｄ），４．４２（１Ｈ，ｓ），３．５７（３Ｈ，ｓ），３．３９−３．３５（１Ｈ，ｍ），３．２３（１Ｈ，ｄ），３．０７（１Ｈ，ｄ)，２．３２（１Ｈ，ｔ），１．９３（１Ｈ，ｄｄ），１．７６（１Ｈ，ｔｄ），０．４６−０．３４（４Ｈ，ｍ） <Production of Compound represented by Formula 6-21>

At room temperature, 2.7 g of 28% sodium methoxide methanol solution and 1.8 g of the compound represented by the formula (8-1) were dissolved in 30 ml of 1,4-dioxane. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 3.8 g of the compound represented by the formula (7-21) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 1 hour. The obtained reaction solution was cooled to 0 ° C., hexane was added, the precipitated crystals were filtered, washed sequentially with tert-butyl methyl ether and hexane, and 4.5 g of the compound represented by the formula (6-21) Got.
1H NMR (CDCl ₃ )
δ ppm: 7.62 (2H, d), 7.45 (2H, d), 4.42 (1H, s), 3.57 (3H, s), 3.39-3.35 (1H, m ), 3.23 (1H, d), 3.07 (1H, d), 2.32 (1H, t), 1.93 (1H, dd), 1.76 (1H, td), 0.46 -0.34 (4H, m)

室温にて、式（６−２１）で示される化合物４．５ｇを水１００ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム３．３７ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄した後、水層に２Ｎ塩酸を加えて酢酸エチルで抽出した。酢酸エチル層を無水硫酸ナトリウムで乾燥後、ろ過し、減圧濃縮し、式（２−２１）で示される化合物の粗生成物３．４ｇを得た。
続いて、窒素雰囲気下、室温にて、式（２−２１）で示される化合物の粗生成物１．７５ｇおよびジメチルアミピリジン３．１３ｇをクロロホルム１４ｍｌとトルエン４ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物３ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−２３）で示される化合物１．９ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５２（２Ｈ，ｄ）、７．３５（２Ｈ，ｄ）、６．９７（２Ｈ，ｓ），５．９９（１Ｈ，ｓ），３．１２（２Ｈ，ｄｄ），２．６５−２．５８（３Ｈ，ｍ），２．４６−２．１３（９Ｈ，ｍ），１．０７（６Ｈ，ｔ），０．６４（４Ｈ，ｓ） <Production of compound represented by formula 1-23>

At room temperature, 4.5 g of the compound represented by the formula (6-21) was dissolved in 100 ml of water. To the resulting solution was added 3.37 g of anhydrous sodium carbonate. The resulting solution was heated to reflux for 5 hours. The reaction mixture was cooled to room temperature, washed with tert-butyl methyl ether, 2N hydrochloric acid was added to the aqueous layer, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain 3.4 g of a crude product of the compound represented by the formula (2-21).
Subsequently, 1.75 g of a crude product of the compound represented by the formula (2-21) and 3.13 g of dimethylamipyridine were dissolved in a mixture of 14 ml of chloroform and 4 ml of toluene at room temperature under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 3 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 1.9 g of a compound represented by the formula (1-23).
1H NMR (CDCl ₃ )
δ ppm: 7.52 (2H, d), 7.35 (2H, d), 6.97 (2H, s), 5.99 (1H, s), 3.12 (2H, dd), 2. 65-2.58 (3H, m), 2.46-2.13 (9H, m), 1.07 (6H, t), 0.64 (4H, s)

窒素雰囲気下、塩化オキサリル８．６ｇと塩化メチレン１５０mlとの混合液を−７８℃まで冷却した後、得られた混合液にジメチルスルホキシド９．４ｇの塩化メチレン６０ｍｌ溶液を滴下し、１０分間攪拌した。その後、得られた混合液に式（２８−１）で示される化合物１０ｇの塩化メチレン２０ｍｌ溶液を滴下し、３０分間攪拌した。その後、得られた混合液にトリエチルアミン３０．４ｇを加え、室温まで昇温し、１時間攪拌した。得られた反応液を１Ｎ塩酸水２００ｍｌに注ぎ、クロロホルムで抽出した。得られた有機層を無水硫酸ナトリウムで乾燥した後、濾過した。得られたろ液を減圧濃縮して式（２９−１）で示される化合物の粗生成物９．８ｇを得た。
引き続き、室温にて、式（２９−１）で示される化合物の粗生成物９．８ｇおよび１−トリフェニルホスホラニリデン−２−プロパノン２２．６ｇをクロロホルム８０ｍｌに溶解した。得られた反応混合溶液を８時間加熱還流した。その後、得られた反応液を減圧下、クロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。続いて、得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（２７−１）で示される化合物７．４ｇを得た(無色油状物質)。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３８−７．２６（５Ｈ，ｍ），６．８２（１Ｈ，ｄｔ），６．１３（１Ｈ，ｄｔ），４．５１（２Ｈ，ｓ），３．６３−３．５７（２Ｈ，ｍ），２．５３（２Ｈ，ｄｄｄ），２．２４（３Ｈ，ｓ） Production Example 1-28: Production of compound represented by formula (1-36) <Production of compound represented by formula 27-1>

In a nitrogen atmosphere, a mixture of 8.6 g of oxalyl chloride and 150 ml of methylene chloride was cooled to −78 ° C., and then a solution of 9.4 g of dimethyl sulfoxide in 60 ml of methylene chloride was added dropwise to the resulting mixture and stirred for 10 minutes. . Thereafter, a solution of 10 g of the compound represented by the formula (28-1) in 20 ml of methylene chloride was added dropwise to the obtained mixed solution, and the mixture was stirred for 30 minutes. Thereafter, 30.4 g of triethylamine was added to the obtained mixture, and the mixture was warmed to room temperature and stirred for 1 hour. The obtained reaction solution was poured into 200 ml of 1N aqueous hydrochloric acid and extracted with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain 9.8 g of a crude product of the compound represented by the formula (29-1).
Subsequently, 9.8 g of a crude product of the compound represented by the formula (29-1) and 22.6 g of 1-triphenylphosphoranylidene-2-propanone were dissolved in 80 ml of chloroform at room temperature. The resulting reaction mixture was heated to reflux for 8 hours. Thereafter, chloroform was removed from the obtained reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. Subsequently, the obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 7.4 g of a compound represented by the formula (27-1) (colorless oily substance).
1H NMR (CDCl ₃ )
δ ppm: 7.38-7.26 (5H, m), 6.82 (1H, dt), 6.13 (1H, dt), 4.51 (2H, s), 3.63-3.57 (2H, m), 2.53 (2H, ddd), 2.24 (3H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液７．７ｇおよび式（８−１）で示される化合物５．３ｇをテトラヒドロフラン１００ｍｌに溶解した。得られた溶液を１５分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（２７−１）で示される化合物７．４ｇを加えた。その後、得られた混合液を１時間加熱還流した。得られた反応液を０℃まで冷却し、ヘキサンを加え、析出した結晶をろ過して、ｔｅｒｔ−ブチルメチルエーテルとヘキサンとで順次洗浄し、式（２５−１）で示される化合物７．２ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３７−７．２６（５Ｈ，ｍ），４．５０−４．３８（３Ｈ，ｍ），３．５９（３Ｈ，ｓ），３．４３−３．４０（３Ｈ， ｍ）,２．８４（１Ｈ，ｄ），２．３２−２．２４（１Ｈ，ｍ），２．０８（１Ｈ，ｄｄ），１．７６（１Ｈ，ｄｄ），１．５７−１．３６（２Ｈ，ｍ） <Production of Compound represented by Formula 25-1>

At room temperature, 7.7 g of 28% sodium methoxide methanol solution and 5.3 g of the compound represented by the formula (8-1) were dissolved in 100 ml of tetrahydrofuran. The resulting solution was heated to reflux for 15 minutes. Thereafter, the heating was stopped, and 7.4 g of the compound represented by the formula (27-1) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 1 hour. The obtained reaction solution was cooled to 0 ° C., hexane was added, the precipitated crystals were filtered, washed sequentially with tert-butyl methyl ether and hexane, and 7.2 g of a compound represented by the formula (25-1). Got.
1H NMR (CDCl ₃ )
δ ppm: 7.37-7.26 (5H, m), 4.50-4.38 (3H, m), 3.59 (3H, s), 3.43-3.40 (3H, m) , 2.84 (1H, d), 2.32-2.24 (1H, m), 2.08 (1H, dd), 1.76 (1H, dd), 1.57-1.36 (2H , M)

室温にて、式（２５−１）で示される化合物３ｇを水９０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム２．９ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、ｔｅｒｔ−ブチルメチルエーテルで洗浄した後、水層に２Ｎ塩酸を加えて酢酸エチルで抽出した。酢酸エチル層を無水硫酸ナトリウムで乾燥後、ろ過し、減圧濃縮し、式（２６−１）で示される化合物の粗生成物２ｇを得た(黄色固体)。
続いて、窒素雰囲気下、室温にて、式（２６−１）で示される化合物の粗生成物７３０ｍｇおよびジメチルアミピリジン１．８ｇをクロロホルム８ｍｌとトルエン２ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．７ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：２）に付し、式（２４−１）で示される化合物８９０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３９−７．２７（５H, ｍ），６．９７（２Ｈ，ｓ），５．７０（１Ｈ，ｓ），４．５３（２H, s）、３．６２−３．５３（２Ｈ，ｍ），２．６９−２．６２（２Ｈ，ｍ），２．５２−２．２２（１０Ｈ，ｍ），１．８３−１．７４（２Ｈ，ｍ），１．０８（６Ｈ，ｄｄｄ） <Production of Compound represented by Formula 24-1>

At room temperature, 3 g of the compound represented by the formula (25-1) was dissolved in 90 ml of water. To the resulting solution was added anhydrous sodium carbonate 2.9 g. The resulting solution was heated to reflux for 5 hours. The reaction mixture was cooled to room temperature, washed with tert-butyl methyl ether, 2N hydrochloric acid was added to the aqueous layer, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain 2 g of a crude product of the compound represented by formula (26-1) (yellow solid).
Subsequently, 730 mg of a crude product of the compound represented by the formula (26-1) and 1.8 g of dimethylamipyridine were dissolved in a mixture of 8 ml of chloroform and 2 ml of toluene at room temperature under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.7 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 2) to obtain 890 mg of a compound represented by the formula (24-1).
1H NMR (CDCl ₃ )
δ ppm: 7.39-7.27 (5H, m), 6.97 (2H, s), 5.70 (1H, s), 4.53 (2H, s), 3.62-3.53 (2H, m), 2.69-2.62 (2H, m), 2.52-2.22 (10H, m), 1.83-1.74 (2H, m), 1.08 (6H) , Ddd)

式（２４−１）で示される化合物４．５ｇにトリエチルアミン１．８ｇの無水テトラヒドロフラン３０ｍｌ溶液を添加した。得られた混合物に氷冷下アセチルクロライド１．８ｇの無水テトラヒドロフラン１０ｍｌ溶液を添加した。得られた混合物を室温下１２時間攪拌した。反応混合物に水を加え、それをクロロホルムで抽出した。抽出したクロロホルム層を無水硫酸ナトリウムで乾燥後、減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（２３−１）で示される化合物３．７ｇを得た（無色油状物質）。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３５−７．２４（５Ｈ，ｍ），６．８８（２Ｈ，ｓ），４．５０（２Ｈ，ｄｄ），３．５６（２Ｈ，ｔ），２．７２−２．２８（１２Ｈ，ｍ），１．８６−１．７３（５Ｈ，ｍ），１．１２−１．０３（６Ｈ，ｍ） <Production of Compound represented by Formula 23-1>

A solution of 1.8 g of triethylamine in 30 ml of anhydrous tetrahydrofuran was added to 4.5 g of the compound represented by the formula (24-1). A solution of 1.8 g of acetyl chloride in 10 ml of anhydrous tetrahydrofuran was added to the resulting mixture under ice cooling. The resulting mixture was stirred at room temperature for 12 hours. Water was added to the reaction mixture and it was extracted with chloroform. The extracted chloroform layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 3.7 g of the compound represented by the formula (23-1). Obtained (colorless oil).
1H NMR (CDCl ₃ )
δ ppm: 7.35-7.24 (5H, m), 6.88 (2H, s), 4.50 (2H, dd), 3.56 (2H, t), 2.72-2.28 (12H, m), 1.86-1.73 (5H, m), 1.12-1.03 (6H, m)

式（２３−１）で示される化合物３．７ｇを酢酸エチル１５０ｍｌに溶解した。得られた混合液へ10％パラジウム炭素１．５ｇを加え、水素下、３５℃で４時間攪拌した。
得られた反応混合液をセライト（登録商標）ろ過し、得られたろ液を減圧濃縮し、式（２２−１）で示される化合物２．４ｇを得た（無色固体）。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：６．８９（２Ｈ，ｓ），３．７９（２Ｈ，ｄ），２．７９−２．６９（３Ｈ，ｍ），２．６０−２．５３（１Ｈ，ｍ），２．４２−２．２５（７Ｈ，ｍ），１．８８（３Ｈ，ｓ），１．８２−１．７３（２Ｈ，ｍ），１．６３−１．６１（２Ｈ，ｍ），１．０７（６Ｈ，ｑ） <Production of Compound represented by Formula 23-1>

3.7 g of the compound represented by the formula (23-1) was dissolved in 150 ml of ethyl acetate. To the obtained mixture, 1.5 g of 10% palladium carbon was added, and the mixture was stirred at 35 ° C. for 4 hours under hydrogen.
The obtained reaction mixture was filtered through Celite (registered trademark), and the obtained filtrate was concentrated under reduced pressure to obtain 2.4 g of a compound represented by the formula (22-1) (colorless solid).
1H NMR (CDCl ₃ )
δ ppm: 6.89 (2H, s), 3.79 (2H, d), 2.79-2.69 (3H, m), 2.60-2.53 (1H, m), 2.42 -2.25 (7H, m), 1.88 (3H, s), 1.82-1.73 (2H, m), 1.63-1.61 (2H, m), 1.07 (6H) , Q)

式（２２−１）で示される化合物３４４ｍｇと式（２１−２）で示される化合物２２７ｍｇをテトラヒドロフラン５ｍｌに溶解した。窒素雰囲気下、室温にて、得られた混合液にトリブチルホフィン２２３ｍｇを滴下し、２時間攪拌した。得られた反応混合液を減圧濃縮し、得られた粗生成物をシリカゲルカラムクロマトグラフィー（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−３６）で示される化合物４００ｍｇを得た。(無色油状物質)
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．２９（１Ｈ，ｄ），６．９６（２Ｈ，ｓ），６．３４（１Ｈ，ｄ），５．８８（１Ｈ，ｓ），２．７１−２．６０（４Ｈ，ｍ），２．４４−２．１６（１３Ｈ，ｍ），１．７０（２Ｈ，ｄｄ），１．１０−１．０１（６Ｈ，ｍ） <Production of Compound represented by Formula 1-36>

344 mg of the compound represented by the formula (22-1) and 227 mg of the compound represented by the formula (21-2) were dissolved in 5 ml of tetrahydrofuran. Under a nitrogen atmosphere, 223 mg of tributylphosphine was added dropwise to the resulting mixture at room temperature, and the mixture was stirred for 2 hours. The obtained reaction mixture was concentrated under reduced pressure, and the resulting crude product was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to give 400 mg of the compound represented by the formula (1-36). Got. (Colorless oily substance)
1H NMR (CDCl ₃ )
δ ppm: 7.29 (1H, d), 6.96 (2H, s), 6.34 (1H, d), 5.88 (1H, s), 2.71-2.60 (4H, m ), 2.44-2.16 (13H, m), 1.70 (2H, dd), 1.10-1.01 (6H, m)

式（２２−１）で示される化合物３４４ｍｇと式（２１−３）で示される化合物１２１ｍｇとをテトラヒドロフラン５ｍｌに溶解した。窒素雰囲気下、室温にて、得られた混合液にトリブチルホフィン１２１ｍｇを滴下し、２時間攪拌した。得られた反応混合液を減圧濃縮し、得られた粗生成物をシリカゲルカラムクロマトグラフィー（溶出液、酢酸エチル：ヘキサン＝１：２）に付し、式（１−３３）で示される化合物８０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．４１（２Ｈ，ｄｄ），７．１３（２Ｈ，ｄｄ），６．９０（１Ｈ，ｓ）、３．０８（２Ｈ，ｔ），２．８２−２．６７（３Ｈ，ｍ），２．５８−２．２４（９Ｈ，ｍ），１．９５−１．８４（３Ｈ，ｍ），１．１３−１．０３（６Ｈ，ｍ） Production Example 1-29: Production of compound represented by formula (1-33) <Production of compound represented by formula 1-33>

344 mg of the compound represented by the formula (22-1) and 121 mg of the compound represented by the formula (21-3) were dissolved in 5 ml of tetrahydrofuran. In a nitrogen atmosphere, at room temperature, 121 mg of tributylphosphine was added dropwise to the obtained mixed solution, and the mixture was stirred for 2 hours. The resulting reaction mixture was concentrated under reduced pressure, and the resulting crude product was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 2) to give 80 mg of the compound represented by the formula (1-33). Got.
1H NMR (CDCl ₃ )
δ ppm: 8.41 (2H, dd), 7.13 (2H, dd), 6.90 (1H, s), 3.08 (2H, t), 2.82-2.67 (3H, m ), 2.58-2.24 (9H, m), 1.95-1.84 (3H, m), 1.13-1.03 (6H, m)

式（２２−１）で示される化合物１７２ｍｇと式（２１−４）で示される化合物１２４ｍｇをテトラヒドロフラン２．５ｍｌに溶解した。窒素雰囲気下、室温にて、得られた混合液にトリブチルホスフィン０．１４ｍｌを滴下し、２時間攪拌した。得られた反応混合液を減圧濃縮し、得られた粗生成物をシリカゲルカラムクロマトグラフィー（溶出液、酢酸エチル：ヘキサン＝１：3→1：2→1：1）に付し、式（１−７６）で示される化合物１６０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．２６−７．２２（２Ｈ，ｍ）、６．９７（２Ｈ，ｓ）、６．６１（２Ｈ，ｄｔ），２．８６−２．８２（２Ｈ，ｍ），２．６７−２．５９（２Ｈ，ｍ），２．４４−２．１８（１０Ｈ，ｍ），１．７３（２Ｈ，ｄｄ），１．１１−１．０２（６Ｈ，ｍ） Production Example 1-30: Production of compound represented by formula (1-76) <Production of compound represented by formula 1-76>

172 mg of the compound represented by the formula (22-1) and 124 mg of the compound represented by the formula (21-4) were dissolved in 2.5 ml of tetrahydrofuran. Under a nitrogen atmosphere, at room temperature, 0.14 ml of tributylphosphine was added dropwise to the resulting mixture, and the mixture was stirred for 2 hours. The obtained reaction mixture was concentrated under reduced pressure, and the resulting crude product was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3 → 1: 2 → 1: 1) to obtain the formula (1 160 mg of the compound represented by -76) was obtained.
1H NMR (CDCl ₃ )
δ ppm: 7.26-7.22 (2H, m), 6.97 (2H, s), 6.61 (2H, dt), 2.86-2.82 (2H, m), 2.67 -2.59 (2H, m), 2.44-2.18 (10H, m), 1.73 (2H, dd), 1.11-1.02 (6H, m)

式（２２−１）で示される化合物３４４ｍｇと式（２１−５）で示される化合物４５６ｍｇとをテトラヒドロフラン５ｍｌに溶解した。窒素雰囲気下、室温にて、得られた混合液にトリブチルホフィン１１１ｍｇを滴下し、２時間攪拌した。得られた反応混合液を減圧濃縮し、得られた粗生成物をシリカゲルカラムクロマトグラフィー（溶出液、酢酸エチル：ヘキサン＝１：４→1：2）に付し、式（１−７７）で示される化合物２１０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．４０（１Ｈ，ｓ），８．６１（１Ｈ，ｄｄ），７．９８−７．９５（２Ｈ，ｍ)，７．６１−７．５１（４Ｈ，ｍ），７．４２（１Ｈ，ｔｄ），７．１１（１Ｈ，ｔｄ）、６．８７（２Ｈ，ｓ），２．８７−２．８３（２Ｈ，ｍ），２．６８−２．５４（３Ｈ，ｍ），２．４６−２．２２（９Ｈ，ｍ），１．８５（３Ｈ，ｓ），１．７９−１．７３（２Ｈ，ｍ），１．０４（６Ｈ，ｄｔ） Production Example 1-31: Production of compound represented by formula (1-77) <Production of compound represented by formula 1-77>

344 mg of the compound represented by the formula (22-1) and 456 mg of the compound represented by the formula (21-5) were dissolved in 5 ml of tetrahydrofuran. Under a nitrogen atmosphere, 111 mg of tributylphosphine was added dropwise to the resulting mixture at room temperature, and the mixture was stirred for 2 hours. The resulting reaction mixture was concentrated under reduced pressure, and the resulting crude product was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4 → 1: 2) to obtain the formula (1-77). 210 mg of the indicated compound was obtained.
1H NMR (CDCl ₃ )
δ ppm: 9.40 (1H, s), 8.61 (1H, dd), 7.98-7.95 (2H, m), 7.61-7.51 (4H, m), 7.42 (1H, td), 7.11 (1H, td), 6.87 (2H, s), 2.87-2.83 (2H, m), 2.68-2.54 (3H, m), 2.46-2.22 (9H, m), 1.85 (3H, s), 1.79-1.73 (2H, m), 1.04 (6H, dt)

室温下、式（１−７７）で示される化合物１５０ｍｇをメタノール２０ｍｌに溶解し、炭酸カリウム１００ｍｇを加え、１時間攪拌した。得られた反応液を減圧濃縮して、式（１−７８）で示される化合物の粗生成物を得た。その後、得られた粗生成物をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−７８）で示される化合物１６０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．３９（１Ｈ，ｓ），８．５９（１Ｈ，ｄｄ，７．９５（２Ｈ、ｍ），７．６０−７．５１（４Ｈ、ｍ），７．４４−７．３９（１Ｈ，ｍ），７．１１（１Ｈ，ｔｄ），６．９４（２Ｈ，ｓ），５．９１（１Ｈ，ｓ），２．８８−２．８３（２Ｈ，ｍ），２．６０−２．５７（２Ｈ，ｍ），２．３２−２．１５（９Ｈ，ｍ），１．７６−１．７１（２H, m），１．０６−０．９７（６Ｈ，ｄｔ） Production Example 1-32: Production of compound represented by formula (1-78) <Production of compound represented by formula 1-78>

At room temperature, 150 mg of the compound represented by the formula (1-77) was dissolved in 20 ml of methanol, 100 mg of potassium carbonate was added, and the mixture was stirred for 1 hour. The obtained reaction solution was concentrated under reduced pressure to obtain a crude product of the compound represented by the formula (1-78). Thereafter, the obtained crude product was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 160 mg of a compound represented by the formula (1-78).
1H NMR (CDCl ₃ )
δ ppm: 9.39 (1H, s), 8.59 (1H, dd, 7.95 (2H, m), 7.60-7.51 (4H, m), 7.44-7.39 ( 1H, m), 7.11 (1H, td), 6.94 (2H, s), 5.91 (1H, s), 2.88-2.83 (2H, m), 2.60-2 .57 (2H, m), 2.32-2.15 (9H, m), 1.76-1.71 (2H, m), 1.06-0.97 (6H, dt)

窒素雰囲気下、０℃にて、テトラメチレンジアミン３．２ｍｌにｎ−ブチルリチウム１６ｍｌ（１．６Ｍヘキサン溶液）を加え、１０分間攪拌した。その後、０℃氷冷下、式(３２−１)で示される化合物５ｇを加えた。その後、得られた溶液を−７８℃まで冷却した後、トリクロロビスマス２．３ｇのテトラヒドロフラン１５ｍｌ懸濁液を加え、室温まで昇温しながら１時間攪拌した。その後、得られた反応液に水２０ｍｌを加え、水層をクロロホルムで抽出した。得られたクロロホルム層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した後、ろ過し、得られたろ液を減圧濃縮して、式（３３−１）で示される化合物の粗生成物２．６ｇを得た。
続いて、室温下、得られた式（３３−１）の粗生成物２．６ｇを脱水クロロホルム２５ｍｌに溶解し、０℃へ冷却した後、塩化スルフリル０．４ｍｌを加えた。その後室温まで昇温し、１時間攪拌した。得られた反応液を減圧濃縮し、得られた油状物質にヘキサンを加え、結晶を析出させ、ろ過することにより、式（３１−１）で示される化合物１．３ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．００（１Ｈ，ｄｄ），７．６６（１Ｈ，ｄｄ），７．５４−７．４６（２Ｈ，ｍ），３．０３（２Ｈ，ｑ），１．３８（３Ｈ，ｔ） Production Example 1-33: Production of compound represented by formula (1-97) <Production of compound represented by formula 31-1>

Under a nitrogen atmosphere, at 0 ° C., 16 ml of n-butyllithium (1.6 M hexane solution) was added to 3.2 ml of tetramethylenediamine and stirred for 10 minutes. Thereafter, 5 g of the compound represented by the formula (32-1) was added under ice-cooling at 0 ° C. Then, after cooling the obtained solution to -78 degreeC, the tetrahydrofuran 15 ml suspension of 2.3 g of trichlorobismuth was added, and it stirred for 1 hour, heating up to room temperature. Thereafter, 20 ml of water was added to the resulting reaction solution, and the aqueous layer was extracted with chloroform. The obtained chloroform layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the obtained filtrate was concentrated under reduced pressure to give a crude product of the compound represented by formula (33-1) 2. 6 g was obtained.
Subsequently, 2.6 g of the obtained crude product of the formula (33-1) was dissolved in 25 ml of dehydrated chloroform at room temperature, cooled to 0 ° C., and 0.4 ml of sulfuryl chloride was added. Thereafter, the mixture was warmed to room temperature and stirred for 1 hour. The obtained reaction liquid was concentrated under reduced pressure, hexane was added to the obtained oily substance, crystals were precipitated, and filtered to obtain 1.3 g of a compound represented by the formula (31-1).
1H NMR (CDCl ₃ )
δ ppm: 8.00 (1H, dd), 7.66 (1H, dd), 7.54-7.46 (2H, m), 3.03 (2H, q), 1.38 (3H, t )

窒素雰囲気下、室温にて、式（３１−１）で示される化合物５５０ｍｇおよび式（２−９）で示される化合物２９０ｍｇをクロロホルム１ｍｌとトルエン４ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液にジアザビシクロウンデセン０．１７ｍｌを加えた。窒素雰囲気下、室温にて得られた混合物を１２時間攪拌した。得られた反応液をクロロホルムで希釈した。得られた希釈液を、ｐＨ１〜２に調整した塩酸水で洗浄し、続いて飽和食塩水で洗浄した。その後、得られた有機層を無水硫酸ナトリウムで乾燥した後、ろ過して、得られたろ液を減圧濃縮し、油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１−９７）で示される化合物２４０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６７（１Ｈ，ｓ），７．６６（１Ｈ，ｄｄ），７．３６−７．２３（４Ｈ，ｍ），７．０４−７．０１（１Ｈ，ｍ），５．９１−５．８７（１Ｈ，ｍ），３．６１−３．５１（１Ｈ，ｍ），３．０８−２．９８（１Ｈ，ｍ），２．７４−２．２８（７Ｈ，ｍ），２．０４−１．９５（１Ｈ，ｍ），１．１７−１．０３（６Ｈ，ｍ） <Production of compound represented by 1-97>

Under a nitrogen atmosphere, at room temperature, 550 mg of the compound represented by formula (31-1) and 290 mg of the compound represented by formula (2-9) were dissolved in a mixture of 1 ml of chloroform and 4 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 0.17 ml of diazabicycloundecene was added to the resulting solution under a nitrogen atmosphere. The resulting mixture was stirred for 12 hours at room temperature under a nitrogen atmosphere. The resulting reaction solution was diluted with chloroform. The obtained diluted solution was washed with aqueous hydrochloric acid adjusted to pH 1-2, and then washed with saturated brine. Thereafter, the obtained organic layer was dried over anhydrous sodium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 240 mg of the compound represented by the formula (1-97).
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, s), 7.66 (1H, dd), 7.36-7.23 (4H, m), 7.04-7.01 (1H, m), 5.91 -5.87 (1H, m), 3.61-3.51 (1H, m), 3.08-2.98 (1H, m), 2.74-2.28 (7H, m), 2 .04-1.95 (1H, m), 1.17-1.03 (6H, m)

室温にて、式（１−１）で示される化合物２５０ｍｇにクロロホルム３ｍｌを加えた。得られた混合物を攪拌しながら０℃まで冷却し、そこにメタクロロ過安息香酸１２０ｍｇをクロロホルム２ｍｌに溶解して得られた混合液を滴下した。得られた混合物を１時間攪拌した。その後、得られた混合物を室温まで加温し、室温で終夜攪拌した。反応液をクロロホルムで希釈して、１０％亜硫酸ナトリウム水溶液で洗浄した。得られたクロロホルム層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した後、濾過した。得られたろ液を減圧濃縮して油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝９：１）に付し、式（１−１９）で示される化合物１５４ｍｇを得た。
１Ｈ ＮＭＲ （ＣＤＣｌ₃）
δ ｐｐｍ ：７．８３−７．７５（４Ｈ，ｍ），６．９７（２Ｈ，ｓ），５．５３（１Ｈ， ｓ），３．０３−２．９４（１Ｈ，ｍ），２．８９−２．６２（３Ｈ， ｍ），２．４６−２．１９（１０Ｈ，ｍ），２．１３−１．７８（２Ｈ，ｍ），１．０８−１．００（６Ｈ， ｍ） Production Example 1-34: Production of compound represented by formula (1-19) <Production of compound represented by formula 1-19>

At room temperature, 3 ml of chloroform was added to 250 mg of the compound represented by the formula (1-1). The obtained mixture was cooled to 0 ° C. with stirring, and a mixture obtained by dissolving 120 mg of metachloroperbenzoic acid in 2 ml of chloroform was added dropwise thereto. The resulting mixture was stirred for 1 hour. The resulting mixture was then warmed to room temperature and stirred at room temperature overnight. The reaction solution was diluted with chloroform and washed with a 10% aqueous sodium sulfite solution. The obtained chloroform layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 9: 1) to obtain 154 mg of a compound represented by the formula (1-19).
1H NMR (CDCl ₃ )
δ ppm: 7.83-7.75 (4H, m), 6.97 (2H, s), 5.53 (1H, s), 3.03-2.94 (1H, m), 2.89 -2.62 (3H, m), 2.46-2.19 (10H, m), 2.13-1.78 (2H, m), 1.08-1.00 (6H, m)

This invention compound manufactured according to manufacture example 1-34 is shown below.
<Compound represented by Formula 1-79>
1H NMR (CDCl ₃ )
δ ppm: 11.51 (1H, s), 8.72 (1H, d), 8.05 (2H, d), 7.60-7.50 (4H, m), 7.31 (1H, d ), 7.19 (1H, t), 6.94 (2H, s), 5.82 (1H, s), 3.34-3.24 (1H, m), 3.09-3.01 ( 1H, m), 2.62-2.55 (2H, m), 2.36-2.14 (10H, m), 1.96-1.80 (2H, m), 1.05-1. 01 (6H, m)
<Compound represented by 1-81>
1H NMR (CDCl ₃ )
δ ppm: 7.83-7.77 (4H, m), 6.90-6.88 (2H, m), 2.99-2.19 (15H, m), 1.35-1.02 ( 9H, m)
<Compound represented by 1-83>
1H NMR (CDCl ₃ )
δ ppm: 8.89 (1H, s), 8.23-8.16 (2H, m), 6.96 (2H, d), 3.36-3.28 (1H, m), 3.01 -2.84 (1H, m), 2.70-2. 21 (13H, m), 1.37-1.17 (3H, m), 1.11-1.03 (6H, m)
<Compound represented by 1-85>
1H NMR (CDCl ₃ )
δ ppm: 8.99 (1H, s), 8.04 (1H, s), 6.97 (2H, s), 5.78 (1H, s), 3.21-3.13 (2H, m ), 2.76-2.65 (2H, m), 2.48-1.82 (12H, m), 1.06-1.02 (6H, m)
<Compound represented by 1-87>
1H NMR (CDCl ₃ )
δ ppm: 7.80 (4H, dd), 6.98 (2H, s), 3.00-2.92 (1H, m), 2.76-2.22 (13H, m), 1.36 -1.33 (6H, m), 1.11-1.05 (6H, m)
<Compound represented by 1-89>
1H NMR (CDCl ₃ )
δ ppm: 8.90 (1H, s), 8.24-8.18 (2H, m), 6.98 (2H, s), 3.24 (1H, dd), 2.89 (1H, dd) ), 2.76-2.67 (2H, m), 2.57-2.23 (10H, m), 1.40-1.35 (6H, m), 1.11-1.05 (6H) , M)
<Compound represented by 1-91>
1H NMR (CDCl ₃ )
δ ppm: 7.84-7.76 (4H, m), 6.98 (1H, s), 5.86 (1H, s), 2.95-2.25 (14H, m), 1.11. -1.06 (6H, m), 1.00-0.94 (1H, m), 0.86-0.74 (2H, s), 0.64-0.59 (1H, s)
<Compound represented by 1-98>
1H NMR (CDCl ₃ )
δ ppm: 7.96-7.93 (4H, m), 6.92 (1H, d), 3.01-2.84 (2H, m), 2.66-2.26 (10H, m) 2.09-1.97 (6H, m), 1.40-1.15 (3H, m)
<Compound represented by Formula 1-154>
1H NMR (CDCl ₃ )
δ ppm: 8.90 (1H, s), 8.24 (1H, dt), 8.18 (1H, dd), 6.98 (2H, s), 5.50 (1H, d), 3. 35-3.19 (1H, m), 3.11-2.99 (1H, m), 2.73-2.64 (2H, m), 2.44-2.23 (12H, m), 1.08-1.03 (6H, m)
<Compound represented by Formula 1-156>
1H NMR (CDCl ₃ )
δ ppm: 9.21 (1H, s), 8.55 (1H, d), 8.12 (1H, dd), 6.97 (2H, s), 5.48 (1H, d), 4. 00 (3H, s), 3.34-3.24 (1H, m), 3.11-3.00 (1H, m), 2.68-2.63 (2H, m), 2.38- 2.06 (12H, m), 1.08-1.01 (6H, m)
<Compound represented by Formula 1-158>
1H NMR (CDCl ₃ )
δ ppm: 8.76 (1H, d), 7.79 (1H, d), 7.45 (1H, dd), 6.97 (2H, s), 5.50 (1H, d), 3. 18-3.14 (2H, m), 2.72-2.65 (2H, m), 2.47-2.24 (11H, m), 2.05-2.01 (1H, m), 1.09-1.02 (6H, m)
<Compound represented by Formula 1-159>
1H NMR (CDCl ₃ )
δ ppm: 9.33 (1H, d), 8.98 (1H, s), 6.98 (2H, s), 5.53 (1H, d), 3.36-3.28 (1H, m ), 3.20-3.11 (1H, m), 2.75-2.66 (2H, m), 2.49-2.20 (11H, m), 1.84-1.63 (1H) , M), 1.08-1.01 (6H, m)
<Compound represented by Formula 1-165>
1H NMR (CDCl ₃ )
δ ppm: 8.39 (1H, dd), 8.12 (1H, dd), 6.97 (2H, s), 5.52 (1H, d), 3.49-3.42 (1H, m ), 3.27-3.20 (1H, m), 2.74-2.64 (2H, m), 2.46-2.14 (11H, m), 1.76-1.66 (1H) , M), 1.08-1.02 (6H, m)

室温にて、式（１−１）で示される化合物２５０ｍｇにクロロホルム３ｍｌを加えた。得られた混合物を撹拌しながら０℃まで冷却し、そこにメタクロロ過安息香酸４４０ｍｇをクロロホルム２ｍｌに溶解して得られた混合液を滴下した。得られた混合物を１時間攪拌した。その後、得られた混合物を室温まで加温し、室温で終夜攪拌した。反応液をクロロホルムで希釈して、得られた希釈液を１０％亜硫酸ナトリウム水溶液で洗浄した。得られたクロロホルム層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した後、濾過した。得られたろ液を減圧濃縮して油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：２）に付し、式（１−２０）で示される化合物１５４ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δｐｐｍ：８．０８（２Ｈ，ｄ），７．８８（２Ｈ，ｄ），６．９７（２Ｈ，ｓ），５．５２（１Ｈ，ｓ），３．２７−３．１５（２Ｈ，ｍ），２．７３−２．６０（２Ｈ，ｍ），２．４５−２．２１（１０Ｈ，ｍ），２．０２−１．９０（２Ｈ，ｍ），１．０８―１．００（６Ｈ，ｍ） Production Example 1-35: Production of compound represented by formula (1-20) <Production of compound represented by formula 1-20>

At room temperature, 3 ml of chloroform was added to 250 mg of the compound represented by the formula (1-1). The obtained mixture was cooled to 0 ° C. with stirring, and a mixture obtained by dissolving 440 mg of metachloroperbenzoic acid in 2 ml of chloroform was added dropwise thereto. The resulting mixture was stirred for 1 hour. The resulting mixture was then warmed to room temperature and stirred at room temperature overnight. The reaction solution was diluted with chloroform, and the resulting diluted solution was washed with a 10% aqueous sodium sulfite solution. The obtained chloroform layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 2) to obtain 154 mg of a compound represented by the formula (1-20).
1H NMR (CDCl ₃ )
δ ppm: 8.08 (2H, d), 7.88 (2H, d), 6.97 (2H, s), 5.52 (1H, s), 3.27-3.15 (2H, m) , 2.73-2.60 (2H, m), 2.45-2.21 (10H, m), 2.02-1.90 (2H, m), 1.08-1.00 (6H, m)

This invention compound manufactured according to manufacture example 1-35 is shown below.
<Compound represented by Formula 1-80>
1H NMR (CDCl ₃ )
δ ppm: 10.46 (1H, s), 8.69 (1H, d), 8.05-7.91 (2H, m), 7.73 (1H, td), 7.64-7.52 (4H, m), 7.34 (1H, td), 6.95 (2H, s), 3.26-3.16 (2H, m), 2.61-2.52 (2H, m), 2.35-1.11 (10H, m), 1.93-1.87 (2H, m), 1.03 (6H, dd)
<Compound represented by Formula 1-82>
1H NMR (CDCl ₃ )
δppm: 8.09 (2H, d), 7.88 (2H, d), 6.98 (2H, s), 3.28-2.99 (2H, m), 2.61-2.21 ( 13H, m), 1.28-1.22 (3H, m), 1.08-1.04 (6H, m)
<Compound represented by Formula 1-84>
1H NMR (CDCl ₃ )
δppm: 9.02 (1H, s), 8.27 (2H, s), 6.98 (2H, s), 5.67 (1H, s), 3.69 (1H, dt), 3.32. (1H, ddd), 2.66-2.21 (13H, m), 1.28-1.24 (3H, m), 1.10-1.02 (6H, m)
<Compound represented by Formula 1-86>
1H NMR (CDCl ₃ )
δppm: 8.79 (1H, s), 8.18 (1H, s), 6.99 (2H, s), 3.86-3.66 (2H, m), 2.86-2.72 ( 2H, m), 2.54-2.09 (12H, m), 1.10-1.01 (6H, m)
<Compound represented by Formula 1-88>
1H NMR (CDCl ₃ )
δppm: 8.09 (2H, d), 7.86 (2H, d), 6.99 (2H, d), 3.11 (2H, dd), 2.68-2.24 (12H, m) , 1.35 (6H, d), 1.08 (6H, dt)
<Compound represented by Formula 1-90>
1H NMR (CDCl ₃ )
δppm: 9.01 (1H, s), 8.27-8.22 (2H, m), 6.98 (2H, s), 3.59-3.49 (2H, m), 2.59- 2.48 (2H, m), 2.59-2.48 (2H, m), 2.42-2.27 (8H, m), 1.33-1.27 (6H, m), 08 (6H, td)
<Compound represented by Formula 1-92>
1H NMR (CDCl ₃ )
δ ppm: 8.08 (2H, d), 7.86 (2H, d), 6.98 (2H, d), 5.86 (1H, s), 3.26-3.08 (2H, m) , 2.88-2.73 (1H, m), 2.68-2.52 (2H, m), 2.47-2.17 (9H, m), 1.12-1.05 (6H, m), 0.83-0.53 (4H, m)
<Compound represented by Formula 1-99>
1H NMR (CDCl ₃ )
δ ppm: 8.09 (2H, d), 7.88 (2H, d), 6.93 (2H, s), 5.59 (1H, s), 3.23 (1H, td), 3.05 -2.98 (1H, m), 2.59-2.23 (9H, m), 2.06-1.97 (6H, m), 1.21 (3H, dt)

式（１−４）で示される化合物５００ｍｇにトリエチルアミン１７５ｍｇの無水テトラヒドロフラン３ｍｌ溶液を添加した。得られた混合物に氷冷下アセチルクロライド１７０ｍｇの無水テトラヒドロフラン１ｍｌ溶液を添加した。得られた混合物を室温下１２時間攪拌した。反応混合物に水５ｍｌを加え、それをクロロホルムで抽出した。得られたクロロホルム層を無水硫酸ナトリウムで乾燥後、減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：６）に付し、式（１−５９）で示される化合物５３０ｍｇを得た（無色油状物質）。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６７（１Ｈ，ｍ），７．６７（１Ｈ，ｄｄ），７．２７（１Ｈ，ｄ），６．８９(２Ｈ，ｓ)，３．３０（２Ｈ，ｔ），２．８４−２．２５（１２Ｈ，ｍ），１．９８−１．８９（５Ｈ，ｍ），１．０９−１．０２（６Ｈ，ｍ） Production Example 1-36: Production of compound represented by formula (1-59) <Production of compound represented by formula 1-59>

A solution of 175 mg of triethylamine in 3 ml of anhydrous tetrahydrofuran was added to 500 mg of the compound represented by the formula (1-4). A solution of 170 mg of acetyl chloride in 1 ml of anhydrous tetrahydrofuran was added to the resulting mixture under ice cooling. The resulting mixture was stirred at room temperature for 12 hours. 5 ml of water was added to the reaction mixture and it was extracted with chloroform. The obtained chloroform layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 6) to obtain 530 mg of a compound represented by the formula (1-59). (Colorless oil).
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, m), 7.67 (1H, dd), 7.27 (1H, d), 6.89 (2H, s), 3.30 (2H, t), 2. 84-2.25 (12H, m), 1.98-1.89 (5H, m), 1.09-1.02 (6H, m)

This invention compound manufactured according to manufacture example 1-36 is shown below.
<Compound represented by Formula 1-60>
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, m), 7.67 (1H, dd), 7.27 (1H, d), 6.88 (2H, s), 3.31 (2H, t), 2. 77-2.23 (12H, m), 2.17-2.11 (2H, m), 1.98-1.88 (2H, m), 1.05 (6H, ddd), 0.84 ( 3H, t)
<Compound represented by Formula 1-61>
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, m), 7.67 (1H, dd), 7.27 (1H, d), 6.87 (2H, s), 3.31 (2H, td), 2. 84-2.25 (12H, m), 1.94 (2H, dt), 1.05 (6H, dt), 0.88 (9H, s)
<Compound represented by Formula 1-62>
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, dd), 7.67 (1H, dd), 7.27 (1H, d), 6.90 (2H, s), 3.70 (3H, s), 3. 31 (2H, t), 2.92-2.26 (12H, m), 1.99-1.89 (2H, m), 1.09-1.02 (6H, m)
<Compound represented by Formula 1-63>
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, dd), 7.67 (1H, dd), 7.27 (1H, d), 6.90 (2H, s), 4.12-4.07 (2H, m ), 3.34-3.27 (2H, m), 2.91-2.27 (12H, m), 1.99-1.88 (2H, m), 1.18 (3H, t), 1.09-1.00 (6H, m)
<Compound represented by Formula 1-66>
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, dd), 7.66 (1H, dd), 7.26 (1H, d), 6.90 (2H, s), 5.80-5.71 (1H, m ), 5.21-5.15 (2H, m), 4.52-4.50 (2H, m), 3.30 (2H, t), 2.82-2.26 (12H, m), 1.97-1.88 (2H, m), 1.09-1.00 (6H, m)
<Compound represented by Formula 1-67>
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, t), 7.66 (1H, dd), 7.35-7.18 (4H, m), 6.95 (2H, s), 6.87-6.83 (2H, m), 3.31 (2H, t), 2.99-2.29 (12H, m), 2.00-1.90 (2H, m), 1.08-1.03 (6H) , M)
<Compound represented by Formula 1-68>
1H NMR (CDCl ₃ )
δ ppm: 8.69 (1H, t), 7.67 (1H, dd), 7.27 (1H, d), 6.93 (2H, s), 3.66-3.27 (2H, m ), 3.06 (1H, dd), 2.84-2.76 (2H, m), 2.56-2.26 (12H, m), 1.99-1.88 (2H, m), 1.14-1.04 (6H, m)
<Compound represented by Formula 1-93>
1H NMR (CDCl ₃ )
δ ppm: 8.91 (1H, s), 8.24-8.18 (2H, m), 6.90 (2H, d), 4.13-4.05 (2H, m), 3.33 (1H, ddd), 3.07-2.24 (14H, m), 1.39-1.02 (12H, m)

６０％水素化ナトリウム１１０ｍｇに無水Ｎ，Ｎ−ジメチルホルムアミド１ｍｌを添加した。得られた混合物に氷冷下、式（１−４）で示される化合物５００ｍｇの無水Ｎ，Ｎ−ジメチルホルムアミド３ｍｌ溶液を滴下した。得られた混合物を氷冷下１０分間攪拌した後、そこにクロロメチル メチル エーテル２００ｍｇの無水Ｎ，Ｎ−ジメチルホルムアミド１ｍｌ溶液を滴下し、得られた混合物を室温下２時間攪拌した。反応混合物に水５ｍｌを加え、それを酢酸エチルで抽出した。得られた酢酸エチル層を水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−６４）で示される化合物２０８ｍｇを得た（黄色油状物質）。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．６７（１Ｈ，ｍ），７．６７（１Ｈ，ｄｄ），７．２７（１Ｈ，ｄ），６．９０(２Ｈ，ｓ)，４．９８（２Ｈ，ｓ），３．３９−３．２２（５Ｈ，ｍ）、３．０３−２．２５（１２Ｈ，ｍ），１．９９−１．８９（２Ｈ，ｍ），１．０８−１．０２（６Ｈ，ｍ） Production Example 1-37: Production of compound represented by formula (1-64) <Production of compound represented by formula 1-64>

1 ml of anhydrous N, N-dimethylformamide was added to 110 mg of 60% sodium hydride. A solution of 500 mg of the compound represented by formula (1-4) in 3 ml of anhydrous N, N-dimethylformamide was added dropwise to the resulting mixture under ice cooling. The resulting mixture was stirred for 10 minutes under ice-cooling, 200 ml of anhydrous N, N-dimethylformamide in 200 mg of chloromethyl methyl ether was added dropwise thereto, and the resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 5 ml of water and it was extracted with ethyl acetate. The obtained ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure, subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4), and the formula (1-64) 208 mg of the indicated compound was obtained (yellow oil).
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, m), 7.67 (1H, dd), 7.27 (1H, d), 6.90 (2H, s), 4.98 (2H, s), 3. 39-3.22 (5H, m), 3.03-2.25 (12H, m), 1.99-1.89 (2H, m), 1.08-1.02 (6H, m)

This invention compound manufactured according to manufacture example 1-37 is shown below.
<Compound represented by Formula 1-65>
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, m), 7.67 (1H, dd), 7.27 (1H, d), 6.91 (2H, s), 5.05-4.99 (2H, m ), 3.56-3.51 (2H, m), 3.37-3.28 (2H, m), 3.04-2.23 (12H, m), 1.97-1.90 (2H) , M), 1.17-0.99 (9H, m)

室温にて、式（１０−３０）で示される化合物７．１０ｇおよびテトラヒドロフラン６０ｍｌを混合、攪拌し、得られた混合物に９５％アクロレイン３．６４ｇとトリエチルアミン１．２１ｇを滴下した。得られた混合物を室温にて５．５時間攪拌した。その後、得られた反応液を減圧濃縮して、式（９−３０）で示される化合物９．３２ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：９．７８（１Ｈ，ｓ），７．６７（１Ｈ，ｄ），７．５４−７．４６（２Ｈ，ｍ），７．３５−７．３１（１Ｈ，ｍ），３．２４（２Ｈ，ｔ），２．８０（２Ｈ，ｄｔ） Production Example 1-38: Production of compound represented by formula (1-30) <Production of compound represented by formula 9-30>

At room temperature, 7.10 g of the compound represented by the formula (10-30) and 60 ml of tetrahydrofuran were mixed and stirred, and 3.64 g of 95% acrolein and 1.21 g of triethylamine were added dropwise to the resulting mixture. The resulting mixture was stirred at room temperature for 5.5 hours. Then, the obtained reaction liquid was concentrated under reduced pressure to obtain 9.32 g of a compound represented by the formula (9-30).
1H NMR (CDCl ₃ )
δ ppm: 9.78 (1H, s), 7.67 (1H, d), 7.54-7.46 (2H, m), 7.35-7.31 (1H, m), 3.24 (2H, t), 2.80 (2H, dt)

室温にて、式（９−３０）で示される化合物９．３２ｇをクロロホルム４０ｍｌに溶解した。得られた溶液に氷冷下トリフェニルホスフィンアセチルメチレン１６．５ｇを加えた。得られた溶液を室温にて、１７時間攪拌した。その後、減圧下、得られた反応液からクロロホルムを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−３０）で示される化合物９．７６ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．６７（１Ｈ，ｄ），７．５２−７．４３（２Ｈ，ｍ），７．３４−７．３０（１Ｈ，ｍ）６．７９（１Ｈ，ｄｔ），６．１１（１Ｈ，ｄｔ），３．１０（２Ｈ，ｔ），２．５７（２Ｈ，ｑｄ），２．２４（３Ｈ，ｓ） <Production of Compound represented by Formula 7-30>

At room temperature, 9.32 g of the compound represented by the formula (9-30) was dissolved in 40 ml of chloroform. 16.5 g of triphenylphosphine acetylmethylene was added to the resulting solution under ice cooling. The resulting solution was stirred at room temperature for 17 hours. Thereafter, chloroform was removed from the resulting reaction solution under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 9.76 g of a compound represented by the formula (7-30).
1H NMR (CDCl ₃ )
δ ppm: 7.67 (1H, d), 7.52-7.43 (2H, m), 7.34-7.30 (1H, m) 6.79 (1H, dt), 6.11 ( 1H, dt), 3.10 (2H, t), 2.57 (2H, qd), 2.24 (3H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液７．５５ｇおよび式（８−１）で示される化合物５．１７ｇをテトラヒドロフラン７０ｍｌに溶解した。得られた溶液を１０分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−３０）で示される化合物９．７６ｇを加えた。その後、得られた混合液を２時間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテル、ヘキサンで順次洗浄し、式（６−３０）で示される化合物６．８０ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：７．７０（１Ｈ，ｄ），７．６１（２Ｈ，ｄｄ），７．３６（１Ｈ，ｑ），４．３９（１Ｈ，ｓ），３．４７（３Ｈ，ｓ），３．１５−３．０８（１Ｈ，ｍ），３．００−２．９３（１Ｈ，ｍ），２．８３（１Ｈ，ｄ），２．３３−２．２３（１Ｈ，ｍ），２．１１（１Ｈ，ｄｄ），１．７７（１Ｈ，ｄｄ），１．５３−１．４４（２Ｈ，ｍ） <Production of Compound represented by Formula 6-30>

At room temperature, 7.55 g of 28% sodium methoxide methanol solution and 5.17 g of the compound represented by the formula (8-1) were dissolved in 70 ml of tetrahydrofuran. The resulting solution was heated to reflux for 10 minutes. Thereafter, the heating was stopped, and 9.76 g of the compound represented by the formula (7-30) was added to the obtained reaction mixture. Thereafter, the obtained mixed solution was heated to reflux for 2 hours. The obtained reaction liquid was cooled to room temperature, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane to obtain 6.80 g of a compound represented by the formula (6-30).
1H NMR (d-DMSO)
δ ppm: 7.70 (1H, d), 7.61 (2H, dd), 7.36 (1H, q), 4.39 (1H, s), 3.47 (3H, s), 3. 15-3.08 (1H, m), 3.00-2.93 (1H, m), 2.83 (1H, d), 2.33-2.23 (1H, m), 2.11 ( 1H, dd), 1.77 (1H, dd), 1.53-1.44 (2H, m)

室温にて、式（６−３０）で示される化合物６．８０ｇを水９０ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム５．７８ｇを加えた。得られた溶液を５時間加熱還流した。反応液を室温まで冷却し、２Ｎ塩酸を加えて酸性にした。得られた反応液を酢酸エチルで抽出して、式（２−３０）で示される化合物６．０１ｇを得た。
窒素雰囲気下、室温にて、式（２−３０）で示される化合物５４１ｍｇおよびジメチルアミノピリジン１．０４ｇをクロロホルム５．０ｍｌとトルエン２．０ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物１．００ｇを加えた。窒素雰囲気下、得られた混合物を７５℃で１．５時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗浄し、無水硫酸ナトリウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（１−３０）で示される化合物３８７ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．６７（１Ｈ，ｄ），７．４９（２Ｈ，ｔ），７．３２−７．２８（１Ｈ，ｍ），６．９８（２Ｈ，ｓ），５．５４（１Ｈ，ｓ），３．０７（２Ｈ，ｄｄｄ），２．６９（２Ｈ，ｔｄ），２．４８−２．２４（１０Ｈ，ｍ），１．８５（２Ｈ，ｑ），１．０８（３Ｈ，ｔ），１．０５（３Ｈ，ｔ） <Production of compound represented by formula 1-30>

At room temperature, 6.80 g of the compound represented by the formula (6-30) was dissolved in 90 ml of water. To the resulting solution was added anhydrous sodium carbonate 5.78 g. The resulting solution was heated to reflux for 5 hours. The reaction mixture was cooled to room temperature and acidified with 2N hydrochloric acid. The obtained reaction solution was extracted with ethyl acetate to obtain 6.01 g of a compound represented by the formula (2-30).
Under a nitrogen atmosphere, at room temperature, 541 mg of the compound represented by the formula (2-30) and 1.04 g of dimethylaminopyridine were dissolved in a mixture of 5.0 ml of chloroform and 2.0 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 1.00 g of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 75 ° C. for 1.5 hours under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 387 mg of the compound represented by the formula (1-30).
1H NMR (CDCl ₃ )
δ ppm: 7.67 (1H, d), 7.49 (2H, t), 7.32-7.28 (1H, m), 6.98 (2H, s), 5.54 (1H, s) ), 3.07 (2H, ddd), 2.69 (2H, td), 2.48-2.24 (10H, m), 1.85 (2H, q), 1.08 (3H, t) , 1.05 (3H, t)

室温にて、式（１０−２９）で示される化合物５．０ｇおよびテトラヒドロフラン５６ｍｌを混合、攪拌し、得られた混合物に９５％アクロレイン２．５６ｇとトリエチルアミン８５２ｍｇを滴下した。得られた混合物を室温にて２時間攪拌した。その後、得られた反応液を減圧濃縮して、式（９−２９）で示される化合物６．６１ｇを得た。
室温にて、式（９−２９）で示される化合物６．６１ｇおよびトリフェニルホスフィンアセチルメチレン１１．６ｇをテトラヒドロフラン２８ｍｌに溶解した。得られた溶液を室温で、５時間攪拌した。その後、減圧下、得られた反応液からテトラヒドロフランを除去した。得られた残渣にｔｅｒｔ−ブチルメチルエーテルおよびヘキサンを加えた。得られた混合物をろ過し、得られたろ液を減圧濃縮した。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：４）に付し、式（７−２９）で示される化合物１．０１ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５６（１Ｈ，ｓ），７．５１−７．４０（３Ｈ，ｍ），６．７８（１Ｈ，ｄｔ），６．１３（１Ｈ，ｄｔ），３．１０（２Ｈ，ｔ），２．５９（２Ｈ，ｑｄ），２．２５（３Ｈ，ｓ） Production Example 1-39: Production of compound represented by formula (1-29) <Production of compound represented by formula 7-29>

At room temperature, 5.0 g of the compound represented by the formula (10-29) and 56 ml of tetrahydrofuran were mixed and stirred, and 2.56 g of 95% acrolein and 852 mg of triethylamine were added dropwise to the resulting mixture. The resulting mixture was stirred at room temperature for 2 hours. Then, the obtained reaction liquid was concentrated under reduced pressure to obtain 6.61 g of a compound represented by the formula (9-29).
At room temperature, 6.61 g of the compound represented by the formula (9-29) and 11.6 g of triphenylphosphine acetylmethylene were dissolved in 28 ml of tetrahydrofuran. The resulting solution was stirred at room temperature for 5 hours. Then, tetrahydrofuran was removed from the obtained reaction liquid under reduced pressure. To the obtained residue, tert-butyl methyl ether and hexane were added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 4) to obtain 1.01 g of a compound represented by the formula (7-29).
1H NMR (CDCl ₃ )
δ ppm: 7.56 (1H, s), 7.51-7.40 (3H, m), 6.78 (1H, dt), 6.13 (1H, dt), 3.10 (2H, t ), 2.59 (2H, qd), 2.25 (3H, s)

室温にて、２８％ナトリウムメトキシドメタノール溶液７８１ｍｇおよび式（８−１）で示される化合物４６４ｍｇをテトラヒドロフラン７ｍｌに溶解した。得られた溶液を１０分間加熱還流した。その後、加熱をやめ、得られた反応混合物に式（７−２９）で示される化合物１．０１ｇを加えた。その後、得られた混合液を１時間加熱還流した。得られた反応液を室温まで冷却し、析出した結晶をろ過により集め、ｔｅｒｔ−ブチルメチルエーテル、ヘキサンで順次洗浄し、式（６−２９）で示される化合物８７３ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５７−７．５１（４Ｈ，ｍ），４．３８（１Ｈ，ｓ），３．４５（３Ｈ，ｓ），３．１０（１Ｈ，ｍ），２．９６（１Ｈ，ｍ），２．８１（１Ｈ，ｄ），２．２８（１Ｈ，ｍ），２．１１（１Ｈ，ｄ），１．７５（１Ｈ，ｔ），１．４７（２Ｈ，ｍ） <Production of compound represented by formula 6-29>

At room temperature, 781 mg of 28% sodium methoxide methanol solution and 464 mg of the compound represented by the formula (8-1) were dissolved in 7 ml of tetrahydrofuran. The resulting solution was heated to reflux for 10 minutes. Thereafter, the heating was stopped, and 1.01 g of the compound represented by the formula (7-29) was added to the obtained reaction mixture. Thereafter, the obtained mixture was heated to reflux for 1 hour. The obtained reaction liquid was cooled to room temperature, and the precipitated crystals were collected by filtration and washed successively with tert-butyl methyl ether and hexane to obtain 873 mg of a compound represented by the formula (6-29).
1H NMR (CDCl ₃ )
δ ppm: 7.57-7.51 (4H, m), 4.38 (1H, s), 3.45 (3H, s), 3.10 (1H, m), 2.96 (1H, m ), 2.81 (1H, d), 2.28 (1H, m), 2.11 (1H, d), 1.75 (1H, t), 1.47 (2H, m)

室温にて、式（６−２９）で示される化合物８７３ｍｇを水１２ｍｌに溶解した。得られた溶液に無水炭酸ナトリウム７４１ｍｇを加えた。得られた溶液を６．５時間加熱還流した。反応液を室温まで冷却し、２Ｎ塩酸を加えて酸性にした。得られた反応液を酢酸エチルで抽出した。酢酸エチル層を減圧濃縮し、得られた結晶をｔｅｒｔ−ブチルメチルエーテルおよびヘキサンで順次洗浄して式（２−２９）で示される化合物４３４ｍｇを得た。
窒素雰囲気下、室温にて、式（２−２９）で示される化合物４３０ｍｇおよびジメチルアミノピリジン８３１ｍｇをクロロホルム４ｍｌとトルエン１ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−１）で示される化合物７９５ｍｇを加えた。窒素雰囲気下、得られた混合物を８０℃で１時間攪拌した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗い、無水硫酸マグネシウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１５：８５）に付し、式（１−２９）で示される化合物１４４ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５６（１Ｈ，ｓ），７．５０−７．４０（３Ｈ，ｍ），６．９８（２Ｈ，ｓ），５．５４（１Ｈ，ｓ），３．１０−３．０１（２Ｈ，ｍ），２．７０（２Ｈ，ｔ），２．４７−２．２４（１０Ｈ，ｍ），１．８６（２Ｈ，ｑ），１．１０−１．０３（６Ｈ，ｍ） <Production of Compound represented by Formula 1-29>

At room temperature, 873 mg of the compound represented by the formula (6-29) was dissolved in 12 ml of water. To the resulting solution, 741 mg of anhydrous sodium carbonate was added. The resulting solution was heated to reflux for 6.5 hours. The reaction mixture was cooled to room temperature and acidified with 2N hydrochloric acid. The resulting reaction solution was extracted with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained crystals were washed successively with tert-butyl methyl ether and hexane to obtain 434 mg of a compound represented by the formula (2-29).
Under a nitrogen atmosphere, at room temperature, 430 mg of the compound represented by the formula (2-29) and 831 mg of dimethylaminopyridine were dissolved in a mixture of 4 ml of chloroform and 1 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 795 mg of the compound represented by the formula (3-1) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was stirred at 80 ° C. for 1 hour under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 15: 85) to obtain 144 mg of the compound represented by the formula (1-29).
1H NMR (CDCl ₃ )
δ ppm: 7.56 (1H, s), 7.50-7.40 (3H, m), 6.98 (2H, s), 5.54 (1H, s), 3.10-3.01 (2H, m), 2.70 (2H, t), 2.47-2.24 (10H, m), 1.86 (2H, q), 1.10-1.03 (6H, m)

窒素雰囲気下、室温にて、１，１′−ビス（ジフェニルホスフィノ）フェロセン−パラジウム（ＩＩ）ジクロリド−ジクロロメタン錯体２．０４ｇ、炭酸セシウム４８．８ｇ、および式（５−１）で示される化合物１０ｇをＮ，Ｎ−ジメチルホルムアミド１２５ｍｌに溶解した。得られた溶液に、トリエチルボラン３２．５ｍｌ（１．０Ｍ ヘキサン溶液）を滴下し、窒素雰囲気下、室温にて１６時間攪拌した。反応液をセライト（登録商標）濾過した後、ろ液に水を加え、ｔｅｒｔ−ブチルメチルエーテルにて抽出し、有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。得られた有機層を減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：１９→１：９）に付し、式（３−１）で示される化合物３．１８ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：６．７８（２Ｈ，ｓ），３．４９（２Ｈ，ｓ），２．５１（２Ｈ，ｑ），２．２３（３Ｈ，ｓ），２．１６（３Ｈ，ｓ），１．２４（３Ｈ，ｔ） Production Example 1-40: Production of compound represented by formula (1-41) <Production of compound represented by formula 3-1>

1,1′-bis (diphenylphosphino) ferrocene-palladium (II) dichloride-dichloromethane complex 2.04 g, cesium carbonate 48.8 g, and a compound represented by formula (5-1) at room temperature under a nitrogen atmosphere 10 g was dissolved in 125 ml of N, N-dimethylformamide. To the obtained solution, 32.5 ml of triethylborane (1.0 M hexane solution) was added dropwise and stirred at room temperature for 16 hours under a nitrogen atmosphere. The reaction mixture was filtered through Celite (registered trademark), water was added to the filtrate, and the mixture was extracted with tert-butyl methyl ether. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The obtained organic layer was concentrated under reduced pressure and subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 19 → 1: 9) to obtain 3.18 g of a compound represented by the formula (3-1). .
1H NMR (CDCl ₃ )
δ ppm: 6.78 (2H, s), 3.49 (2H, s), 2.51 (2H, q), 2.23 (3H, s), 2.16 (3H, s), 1. 24 (3H, t)

室温にて、式（１２−４）で示される化合物３．１８ｇを水２５ｍｌに溶解した。得られた溶液に４８％ 臭化水素酸２６．６ｍｌ加え、４０℃で１５分間攪拌した。得られた反応液に、０℃で２．３４Ｍ 亜硝酸ナトリウム水溶液１０ｍｌを滴下し、氷冷下２０分間攪拌した。得られた混合物を、硫酸銅（ＩＩ）五水和物３．１９ｇと銅（粉末）１．２７ｇとに４８％臭化水素酸２６．６ｍｌを加え０℃に冷却した混合物に、滴下した。得られた溶液を室温にて、３．５時間攪拌した。得られた反応液をセライト（登録商標）濾過し、得られたろ液を酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。得られた有機層を減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、ヘキサン）に付し、式（１１−４）で示される化合物１．９１ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：６．９０（１Ｈ，ｓ），６．８８（１Ｈ，ｓ），２．７４（２Ｈ，ｑ），２．３８（３Ｈ，ｓ），２．２５（３Ｈ，ｓ），１．２１（３Ｈ，ｔ） <Production of Compound represented by Formula 11-4>

At room temperature, 3.18 g of the compound represented by the formula (12-4) was dissolved in 25 ml of water. To the obtained solution, 26.6 ml of 48% hydrobromic acid was added and stirred at 40 ° C. for 15 minutes. To the obtained reaction solution, 10 ml of a 2.34M sodium nitrite aqueous solution was added dropwise at 0 ° C., and the mixture was stirred for 20 minutes under ice cooling. The obtained mixture was added dropwise to a mixture obtained by adding 26.6 ml of 48% hydrobromic acid to 3.19 g of copper (II) sulfate pentahydrate and 1.27 g of copper (powder) and cooling to 0 ° C. The resulting solution was stirred at room temperature for 3.5 hours. The obtained reaction solution was filtered through Celite (registered trademark), and the obtained filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The obtained organic layer was concentrated under reduced pressure and subjected to silica gel column chromatography (eluent, hexane) to obtain 1.91 g of a compound represented by the formula (11-4).
1H NMR (CDCl ₃ )
δ ppm: 6.90 (1H, s), 6.88 (1H, s), 2.74 (2H, q), 2.38 (3H, s), 2.25 (3H, s), 1. 21 (3H, t)

窒素雰囲気下、室温にて、式（１１−４）で示される化合物１．９１ｇをテトラヒドロフラン２３ｍｌに溶解した。得られた溶液を−７８℃まで冷却し窒素雰囲気下、ｎ−ブチルリチウム（１．６３Ｍ ヘキサン溶液）を滴下した。その後、窒素雰囲気下、反応液を４０℃で４時間攪拌した。得られた溶液を−７８℃まで冷却し、窒素雰囲気下トリメトキシボラン１．１２ｇを滴下し、室温にて２３時間攪拌した。得られた溶液を０℃まで冷却し、１Ｎ 塩酸を加えて酸性にした。得られた反応液をクロロホルムで抽出し、有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。有機層を減圧濃縮後、濾過し残渣をヘキサンで洗浄することで、式（３−４）で示される化合物６５４ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：６．８６（１Ｈ，ｓ），６．８５（１Ｈ，ｓ），４．５８（２Ｈ，ｄ），２．６３（２Ｈ，ｑ），２．３５（３Ｈ，ｓ），２．２９（３Ｈ，ｓ），１．２３（３Ｈ，ｔ） <Production of compound represented by formula 3-4>

1.91 g of the compound represented by the formula (11-4) was dissolved in 23 ml of tetrahydrofuran at room temperature under a nitrogen atmosphere. The obtained solution was cooled to −78 ° C., and n-butyllithium (1.63 M hexane solution) was added dropwise under a nitrogen atmosphere. Thereafter, the reaction solution was stirred at 40 ° C. for 4 hours under a nitrogen atmosphere. The obtained solution was cooled to −78 ° C., 1.12 g of trimethoxyborane was added dropwise under a nitrogen atmosphere, and the mixture was stirred at room temperature for 23 hours. The resulting solution was cooled to 0 ° C. and acidified with 1N hydrochloric acid. The resulting reaction solution was extracted with chloroform, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, filtered, and the residue was washed with hexane to obtain 654 mg of the compound represented by the formula (3-4).
1H NMR (CDCl ₃ )
δ ppm: 6.86 (1H, s), 6.85 (1H, s), 4.58 (2H, d), 2.63 (2H, q), 2.35 (3H, s), 2. 29 (3H, s), 1.23 (3H, t)

窒素雰囲気下、室温にて、四酢酸鉛１．８７ｇ、酢酸水銀５８．５ｍｇおよび式（５−４）で示される化合物６５４ｍｇをクロロホルム７ｍｌに溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、反応液を４５℃で４時間攪拌した。反応液を室温まで冷却し、セライト（登録商標）濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質にヘキサンを加え、得られた混合物を減圧濃縮して黄色固体を得た。窒素雰囲気下、室温にて、得られた固体をクロロホルム１６ｍｌに溶解した。得られた溶液に炭酸カリウム６．０９ｇを加え、１５分間攪拌した。その後、反応液をセライト（登録商標）濾過した。得られたろ液を減圧濃縮し、式（３−４）で示される化合物２１ｇを得た。
窒素雰囲気下、室温にて、式（２−１）で示される化合物３３２ｍｇおよびジメチルアミノピリジン６４４ｍｇをクロロホルム３ｍｌとトルエン１ｍｌとの混合物に溶解した。得られた溶液を窒素雰囲気下、室温にて１５分間攪拌した。その後、窒素雰囲気下、得られた溶液に式（３−４）で示される化合物６００ｍｇを加えた。窒素雰囲気下、得られた混合物を２時間加熱還流した。得られた反応液を室温まで冷却し、２Ｎ塩酸でｐＨ１になるように調整し、セライト（登録商標）濾過した。得られたろ液をクロロホルムで抽出した。得られたクロロホルム層を水で洗浄し、無水硫酸マグネシウムで乾燥し、濾過した。得られたろ液を減圧濃縮して黄色油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：９→３：１７）に付し、式（１−４１）で示される化合物３６１ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５４（２Ｈ，ｄ），７．３７（２Ｈ，ｄ），６．９６（２Ｈ，ｓ），５．５０（１Ｈ，ｓ），３．１３−３．０３（２Ｈ，ｍ），２．７１（２Ｈ，ｔ），２．４７−２．２５（８Ｈ，ｍ），２．０６−２．００（３Ｈ，ｍ），１．９０−１．８５（２Ｈ，ｍ），１．１０−１．０２（３Ｈ，ｍ） <Production of compound represented by formula 1-41>

Under a nitrogen atmosphere, at room temperature, 1.87 g of lead tetraacetate, 58.5 mg of mercury acetate and 654 mg of the compound represented by the formula (5-4) were dissolved in 7 ml of chloroform. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, the reaction solution was stirred at 45 ° C. for 4 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature and filtered through Celite (registered trademark). The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. Hexane was added to the obtained oily substance, and the resulting mixture was concentrated under reduced pressure to obtain a yellow solid. The obtained solid was dissolved in 16 ml of chloroform at room temperature under a nitrogen atmosphere. To the resulting solution, 6.09 g of potassium carbonate was added and stirred for 15 minutes. Thereafter, the reaction solution was filtered through Celite (registered trademark). The obtained filtrate was concentrated under reduced pressure to obtain 21 g of a compound represented by the formula (3-4).
Under a nitrogen atmosphere, at room temperature, 332 mg of the compound represented by formula (2-1) and 644 mg of dimethylaminopyridine were dissolved in a mixture of 3 ml of chloroform and 1 ml of toluene. The resulting solution was stirred at room temperature for 15 minutes under a nitrogen atmosphere. Thereafter, 600 mg of the compound represented by the formula (3-4) was added to the obtained solution under a nitrogen atmosphere. The resulting mixture was heated to reflux for 2 hours under a nitrogen atmosphere. The resulting reaction solution was cooled to room temperature, adjusted to pH 1 with 2N hydrochloric acid, and filtered through Celite (registered trademark). The obtained filtrate was extracted with chloroform. The obtained chloroform layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a yellow oily substance. The obtained oil was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 9 → 3: 17) to obtain 361 mg of the compound represented by the formula (1-41).
1H NMR (CDCl ₃ )
δ ppm: 7.54 (2H, d), 7.37 (2H, d), 6.96 (2H, s), 5.50 (1H, s), 3.13-3.03 (2H, m ), 2.71 (2H, t), 2.47-2.25 (8H, m), 2.06-2.00 (3H, m), 1.90-1.85 (2H, m), 1.10-1.02 (3H, m)

This invention compound manufactured according to manufacture example 1-40 is shown below.
<Production of Compound represented by Formula 1-128>
1H NMR (CDCl ₃ )
δ ppm: 7.53 (2H, d), 7.37 (3H, d), 7.23-7.12 (3H, m), 3.05 (2H, td), 2.69 (2H, d ), 2.47-2.30 (3H, m), 1.87-1.81 (2H, m)
<Production of compound represented by formula 1-167>
1H NMR (CDCl ₃ )
δ ppm: 7.55-7.49 (3H, m), 7.38-7.26 (3H, m), 7.19-7.14 (1H, m), 5.62 (1H, s) , 3.07-3.06 (2H, m), 2.72-2.63 (2H, m), 2.48-2. 21 (3H, m), 1.87 (2H, dt)
<Production of Compound represented by Formula 1-168>
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, s), 7.70-7.65 (2H, m), 7.38 (1H, tt), 7.29-7.23 (2H, m), 7.16 (1H, ddd), 5.58 (1H, d), 3.31 (2H, t), 2.81-2.67 (2H, m), 2.55-2.24 (3H, m), 1.97-1.88 (2H, m)
<Production of Compound represented by Formula 1-170>
1H NMR (CDCl ₃ )
δ ppm: 8.63 (1H, s), 7.66 (1H, dd), 7.25 (1H, d), 6.61 (2H, s), 3.25-3.21 (2H, m ), 2.69 (2H, d), 2.37-2.31 (3H, m), 1.86-1.83 (2H, m)
<Production of Compound represented by Formula 1-171>
1H NMR (CDCl ₃ )
δ ppm: 7.69 (1H, ddd), 7.54 (2H, d), 7.38 (3H, d), 7.28-7.13 (2H, m), 5.58 (1H, s) ), 3.07 (2H, q), 2.77-2.25 (5H, m), 1.91-1.85 (2H, m)

窒素雰囲気下、室温にて式（３２−２）で示される化合物２．５２ｇをテトラヒドロフラン１５ｍｌに溶解した。得られた溶液を−７８℃に冷却し、ｎ−ブチルリチウム1０ml（１．６Ｍヘキサン溶液）を加え、１時間攪拌した。その後、トリクロロビスマス１．４４ｇのテトラヒドロフラン１０ｍｌ懸濁液を加え、室温まで昇温しながら約１時間攪拌した。得られた反応液へ水２０ｍｌを加え、セライト（登録商標）濾過した。ろ液をクロロホルムで抽出した。得られたクロロホルム層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、ろ過し、得られたろ液を減圧濃縮して、式（３３−２）で示される化合物の粗生成物２．１８ｇを得た。
続いて、室温下、得られた式（３３−２）で示される化合物の粗生成物２．１８ｇを脱水クロロホルム５ｍｌに溶解し、０℃まで冷却した後、塩化スルフリル０．５５ｍｌを加えた。その後室温まで昇温し、３０分間攪拌した。得られた反応液にｔｅｒｔ−ブチルメチルエーテルを加え結晶を析出させた後、減圧濃縮し、ろ過することにより、式（３１−２）で示される化合物１．８６ｇを得た。
１Ｈ ＮＭＲ（ｄ‐ＤＭＳＯ）
δ ｐｐｍ：８．０３（３Ｈ，ｄｄ）、７．６２（３Ｈ，ｔ）、７．５１（３Ｈ，ｄ）、７．３４（３Ｈ，ｔ）、３．８２（９Ｈ，ｓ） Production Example 1-41: Production of compound represented by formula (1-105) <Production of compound represented by formula 31-2>

In a nitrogen atmosphere, 2.52 g of the compound represented by the formula (32-2) was dissolved in 15 ml of tetrahydrofuran at room temperature. The obtained solution was cooled to −78 ° C., 10 ml of n-butyllithium (1.6M hexane solution) was added, and the mixture was stirred for 1 hour. Thereafter, a suspension of 1.44 g of trichlorobismuth in 10 ml of tetrahydrofuran was added, and the mixture was stirred for about 1 hour while raising the temperature to room temperature. 20 ml of water was added to the resulting reaction solution, and filtered through Celite (registered trademark). The filtrate was extracted with chloroform. The obtained chloroform layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the obtained filtrate was concentrated under reduced pressure to give a crude product of the compound represented by formula (33-2) 2. 18 g was obtained.
Subsequently, 2.18 g of the obtained crude product of the compound represented by the formula (33-2) was dissolved in 5 ml of dehydrated chloroform at room temperature, cooled to 0 ° C., and then 0.55 ml of sulfuryl chloride was added. Thereafter, the temperature was raised to room temperature and stirred for 30 minutes. After adding tert-butyl methyl ether to the obtained reaction liquid to precipitate crystals, the reaction liquid was concentrated under reduced pressure and filtered to obtain 1.86 g of the compound represented by the formula (31-2).
1H NMR (d-DMSO)
δ ppm: 8.03 (3H, dd), 7.62 (3H, t), 7.51 (3H, d), 7.34 (3H, t), 3.82 (9H, s)

窒素雰囲気下、室温にて、式（２−９）で示される化合物４７５ｍｇ、１,８‐ジアザビシクロ[５.４.０]ウンデカ‐７‐エン２７４ｍｇ、および式（３１−２）で示される化合物１，０８ｇをクロロホルム１ｍｌとトルエン５ｍｌとの混合物に溶解し、窒素雰囲気下、室温にて２４時間攪拌した。得られた反応液をクロロホルムで希釈し、ｐＨ１〜２に調整した塩酸水で洗浄し、続いて飽和食塩水で洗浄した。その後、得られた有機層を無水硫酸マグネシウムで乾燥した後、ろ過して、得られたろ液を減圧濃縮し、油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：９→３：７）に付し、式（１−１０５）で示される化合物７２．４ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５３（２Ｈ，ｄ），７．３８−７．３４（３Ｈ，ｍ），７．１４−６．９８（３Ｈ，ｍ），６．３０（１Ｈ，ｓ），３．８０（３Ｈ，ｓ），３．１０−３．０２（２Ｈ，ｍ），２．７３−２．６５（２Ｈ，ｍ），２．４７−２．３９（２Ｈ，ｍ），２．３１−２．２４（１Ｈ，ｍ），１．８８−１．８２（２Ｈ，ｍ） <Production of compound represented by 1-105>

475 mg of the compound represented by the formula (2-9) at room temperature under nitrogen atmosphere, 274 mg of 1,8-diazabicyclo [5.4.0] undec-7-ene, and the compound represented by the formula (31-2) 1,08 g was dissolved in a mixture of chloroform (1 ml) and toluene (5 ml) and stirred at room temperature for 24 hours under a nitrogen atmosphere. The obtained reaction solution was diluted with chloroform, washed with aqueous hydrochloric acid adjusted to pH 1-2, and then washed with saturated brine. Thereafter, the obtained organic layer was dried over anhydrous magnesium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oil was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 9 → 3: 7) to obtain 72.4 mg of the compound represented by the formula (1-105).
1H NMR (CDCl ₃ )
δ ppm: 7.53 (2H, d), 7.38-7.34 (3H, m), 7.14-6.98 (3H, m), 6.30 (1H, s), 3.80 (3H, s), 3.10-3.02 (2H, m), 2.73-2.65 (2H, m), 2.47-2.39 (2H, m), 2.31-2 .24 (1H, m), 1.88-1.82 (2H, m)

窒素雰囲気下、室温にて式（３２−３）で示される化合物３．２０ｇをテトラヒドロフラン１５ｍｌに溶解した。得られた溶液を−７８℃に冷却し、ｎ−ブチルリチウム1０ml（１．６Ｍヘキサン溶液）を加え、１時間攪拌した。その後、テトラヒドロフラン１０ｍｌに懸濁したトリクロロビスマス１．４４ｇ溶液を加え、室温まで昇温しながら１時間攪拌した。得られた反応液へ水２０ｍｌを加え、水層をクロロホルムで抽出した。得られたクロロホルム層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、ろ過し、得られたろ液を減圧濃縮して、式（３３−３）で示される化合物の粗生成物３．０７ｇを得た。
続いて、室温下、得られた式（３３−３）で示される化合物の粗生成物３．０７ｇを脱水クロロホルム５ｍｌに溶解し、０℃に冷却した後、塩化スルフリル０．５５ｍｌを加えた。その後室温まで昇温し、３０分間攪拌した。得られた反応液を減圧濃縮し、得られた油状物質にヘキサンを加え、結晶を析出させた。得られた結晶をろ過することにより、式（３１−３）で示される化合物１．２５ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．１１（３Ｈ，ｄ）、７．５１−７．４５（９Ｈ，ｍ）、７．３０（６Ｈ、ｄ）、７．１９−７．１５（３Ｈ、ｍ）、７．０５（６Ｈ，ｔ） Production Example 1-42: Production of compound represented by formula (1-96) <Production of compound represented by formula 31-3>

Under a nitrogen atmosphere, 3.20 g of the compound represented by the formula (32-3) was dissolved in 15 ml of tetrahydrofuran at room temperature. The obtained solution was cooled to −78 ° C., 10 ml of n-butyllithium (1.6M hexane solution) was added, and the mixture was stirred for 1 hour. Thereafter, a solution of 1.44 g of trichlorobismuth suspended in 10 ml of tetrahydrofuran was added, followed by stirring for 1 hour while raising the temperature to room temperature. 20 ml of water was added to the resulting reaction solution, and the aqueous layer was extracted with chloroform. 2. The obtained chloroform layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the obtained filtrate was concentrated under reduced pressure to give a crude product of the compound represented by the formula (33-3). 07 g was obtained.
Subsequently, 3.07 g of the resulting crude product of the compound represented by the formula (33-3) obtained at room temperature was dissolved in 5 ml of dehydrated chloroform, cooled to 0 ° C., and 0.55 ml of sulfuryl chloride was added. Thereafter, the temperature was raised to room temperature and stirred for 30 minutes. The obtained reaction liquid was concentrated under reduced pressure, and hexane was added to the obtained oily substance to precipitate crystals. By filtering the obtained crystals, 1.25 g of a compound represented by the formula (31-3) was obtained.
1H NMR (CDCl ₃ )
δ ppm: 8.11 (3H, d), 7.51-7.45 (9H, m), 7.30 (6H, d), 7.19-7.15 (3H, m), 7.05 (6H, t)

窒素雰囲気下、室温にて、式（２−９）で示される化合物３．１６ｍｇ、１,８‐ジアザビシクロ［５．４．０］ウンデカ‐７‐エン１８３ｍｇ、および式（３１−３）で示される化合物８８７ｍｇをクロロホルム１ｍｌとトルエン４ｍｌとの混合物に溶解し、窒素雰囲気下、室温にて２４時間攪拌した。得られた反応液をクロロホルムで希釈し、得られた希釈液を、ｐＨ１〜２に調整した塩酸水で洗浄し、続いて飽和食塩水で洗浄した。その後、得られた有機層を無水硫酸マグネシウムで乾燥した後、ろ過して、得られたろ液を減圧濃縮し、油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝３：７）に付し、式（１−９６）で示される化合物９９ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５４−７．１７（１３Ｈ，ｍ），５．６６（１Ｈ，ｓ），３．０２（２Ｈ，ｍ），２，７３（２Ｈ，ｍ），２．５９−２．１７（３Ｈ，ｍ），１．８２−１．７７（２Ｈ，ｍ） <Production of compound represented by 1-96>

3.16 mg of the compound represented by the formula (2-9), 1,8-diazabicyclo [5.4.0] undec-7-ene 183 mg, and the formula (31-3) at room temperature under a nitrogen atmosphere 887 mg of the above compound was dissolved in a mixture of 1 ml of chloroform and 4 ml of toluene and stirred at room temperature for 24 hours under a nitrogen atmosphere. The obtained reaction liquid was diluted with chloroform, and the obtained diluted liquid was washed with aqueous hydrochloric acid adjusted to pH 1-2, and then washed with saturated saline. Thereafter, the obtained organic layer was dried over anhydrous magnesium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 3: 7) to obtain 99 mg of a compound represented by the formula (1-96).
1H NMR (CDCl ₃ )
δ ppm: 7.54-7.17 (13H, m), 5.66 (1H, s), 3.02 (2H, m), 2, 73 (2H, m), 2.59-2.17 (3H, m), 1.82-1.77 (2H, m)

This invention compound manufactured according to manufacture example 1-42 is shown below.
<Production of compound represented by formula 1-42>
1H NMR (CDCl ₃ )
δ ppm: 7.79 (1H, d), 7.63-7.53 (4H, m), 7.38 (2H, d), 7.20 (1H, dd), 5.40 (1H, s) ), 3.06 (2H, t), 2.75-2.25 (5H, m), 1.86 (2H, dt)
<Production of Compound represented by Formula 1-166>
1H NMR (CDCl ₃ )
δ ppm: 7.54 (2H, d), 7.38 (2H, d), 7.31-7.06 (2H, m), 7.04 (1H, m), 5.65 (1H, d ), 3.11-3.03 (2H, m), 2.75-2.65 (2H, m), 2.49-2.39 (2H, m), 2.32-2.23 (1H) , M), 2.11 (3H, d), 1.87 (2H, q)

窒素雰囲気下、氷冷下にてジエチル亜鉛２０ｍｌ（１．０Ｍヘキサン溶液）をジクロロメタン２０ｍｌに溶解させ、トリフルオロ酢酸２．２８ｇのジクロロメタン２０ｍｌ溶液を添加した。得られた混合液を氷冷下、２０分間攪拌した後、ジヨードメタン５．３６ｇのジクロロメタン２０ｍｌ溶液を添加し、２０分間攪拌した。得られた溶液に氷冷下、２−ブロモスチレン１．８３ｇのジクロロメタン１０ｍｌ溶液を加え、室温にて6時間攪拌した。得られた反応液に２Ｎ塩酸水を加えｐＨ１〜２とした後、ヘキサンで抽出した。有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、ろ過し、得られたろ液を減圧濃縮して、式（３２−４）で示される化合物の粗生成物１．７６ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５４（１Ｈ，ｄｄ）、７．２０（１Ｈ，ｔｄ）、７．０２（１Ｈ、ｔｄ）、６．９３（１Ｈ、ｄｄ）、２．１６（１Ｈ，ｔｔ）、１．０１（２Ｈ，ｄｄｄ）、０．６８（２Ｈ，ｄｔ） Production Example 1-43: Production of compound represented by formula (1-102) <Production of compound represented by 32-4>

Under a nitrogen atmosphere, 20 ml of diethylzinc (1.0 M hexane solution) was dissolved in 20 ml of dichloromethane under ice cooling, and a solution of 2.28 g of trifluoroacetic acid in 20 ml of dichloromethane was added. The resulting mixture was stirred for 20 minutes under ice cooling, then a solution of 5.36 g of diiodomethane in 20 ml of dichloromethane was added and stirred for 20 minutes. Under ice cooling, a solution of 1.83 g of 2-bromostyrene in 10 ml of dichloromethane was added to the resulting solution, and the mixture was stirred at room temperature for 6 hours. 2N hydrochloric acid was added to the resulting reaction solution to adjust the pH to 1-2, followed by extraction with hexane. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain 1.76 g of a crude product of the compound represented by formula (32-4). It was.
1H NMR (CDCl ₃ )
δ ppm: 7.54 (1H, dd), 7.20 (1H, td), 7.02 (1H, td), 6.93 (1H, dd), 2.16 (1H, tt), 1. 01 (2H, ddd), 0.68 (2H, dt)

窒素雰囲気下、室温にて式（３２−４）で示される化合物１．７６ｇをテトラヒドロフラン９ｍｌへ溶解した。得られた溶液を−７８℃に冷却し、ｎ−ブチルリチウム６．６ｍｌ（１．６Ｍヘキサン溶液）を加え、３０分間攪拌した。その後、得られた混合物に、トリクロロビスマス９３９ｍｇのテトラヒドロフラン５ｍｌ懸濁液を加え、室温まで昇温しながら１時間攪拌した。得られた反応液に水２０ｍｌを加え、クロロホルムで抽出した。得られたクロロホルム層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後ろ過し、得られたろ液を減圧濃縮して、式（３３−４）で示される化合物の粗生成物２．２７ｇを得た。
続いて、室温下、得られた式（３３−４）で示される化合物の粗生成物２．２７ｇを脱水クロロホルム５ｍｌに溶解し、０℃に冷却した後、塩化スルフリル０．３６ｍｌを加えた。その後室温まで昇温し、１時間攪拌した。得られた反応液にｔｅｒｔ−ブチルメチルエーテルを加え結晶を析出させた後、減圧濃縮した。得られた結晶をろ過することにより、式（３１−４）で示される化合物１．０５ｇを得た。
１Ｈ ＮＭＲ（ｄ−ＤＭＳＯ）
δ ｐｐｍ：７．９２（３Ｈ，ｔ）、７．５８−７．５２（６Ｈ，ｍ）、７．２６（３Ｈ、ｔ）、２．３６−２．２８（３Ｈ、ｍ）、１．０３−０．９４（１２Ｈ，ｍ） <Production of compound represented by 31-4>

Under a nitrogen atmosphere, 1.76 g of the compound represented by the formula (32-4) was dissolved in 9 ml of tetrahydrofuran at room temperature. The obtained solution was cooled to −78 ° C., 6.6 ml of n-butyllithium (1.6 M hexane solution) was added, and the mixture was stirred for 30 minutes. Thereafter, a suspension of 939 mg of trichlorobismuth in 5 ml of tetrahydrofuran was added to the resulting mixture, and the mixture was stirred for 1 hour while warming to room temperature. 20 ml of water was added to the resulting reaction solution and extracted with chloroform. The obtained chloroform layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure to obtain 2.27 g of a crude product of the compound represented by the formula (33-4). Got.
Subsequently, 2.27 g of the obtained crude product of the compound represented by the formula (33-4) was dissolved in 5 ml of dehydrated chloroform at room temperature, cooled to 0 ° C., and 0.36 ml of sulfuryl chloride was added. Thereafter, the mixture was warmed to room temperature and stirred for 1 hour. To the resulting reaction solution was added tert-butyl methyl ether to precipitate crystals, which were then concentrated under reduced pressure. By filtering the obtained crystals, 1.05 g of the compound represented by the formula (31-4) was obtained.
1H NMR (d-DMSO)
δ ppm: 7.92 (3H, t), 7.58-7.52 (6H, m), 7.26 (3H, t), 2.36-2.28 (3H, m), 1.03 -0.94 (12H, m)

窒素雰囲気下、室温にて、式（２−９）で示される化合物３．１６ｍｇ、１，８‐ジアザビシクロ［５．４．０］ウンデカ‐７‐エン１８３ｍｇ、および式（３１−４）で示される化合物８８７ｍｇをクロロホルム１ｍｌとトルエン４ｍｌとの混合物に溶解した。窒素雰囲気下、室温にて得られた混合物を約２４時間攪拌した。得られた反応液をクロロホルムで希釈し、ｐＨ１〜２に調整した塩酸水で洗浄し、続いて飽和食塩水で洗浄した。その後、得られた有機層を無水硫酸マグネシウムで乾燥した後、ろ過して、得られたろ液を減圧濃縮し、油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝３：７）に付し、式（１−１０２）で示される化合物５６ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．５４（２Ｈ，ｄ），７．３８−７．２２（４Ｈ，ｍ），７．０６−７．００（２Ｈ，ｍ），５．７６（１Ｈ，ｄ），３．０８−３．０２（２Ｈ，ｍ），２．７５−２．６８（２Ｈ，ｍ），２．５５−２．１０（４Ｈ，ｍ），１．９０−１．８６（２Ｈ，ｍ），０．８７−０．６５（３Ｈ，ｍ）、０．５７−０．４７（１Ｈ，ｍ） <Production of compound represented by 1-102>

In a nitrogen atmosphere at room temperature, 3.16 mg of the compound represented by formula (2-9), 1,8-diazabicyclo [5.4.0] undec-7-ene 183 mg, and formula (31-4) 887 mg of the above compound was dissolved in a mixture of 1 ml of chloroform and 4 ml of toluene. The resulting mixture was stirred at room temperature for about 24 hours under a nitrogen atmosphere. The obtained reaction solution was diluted with chloroform, washed with aqueous hydrochloric acid adjusted to pH 1-2, and then washed with saturated brine. Thereafter, the obtained organic layer was dried over anhydrous magnesium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain an oily substance. The obtained oily substance was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 3: 7) to obtain 56 mg of the compound represented by the formula (1-102).
1H NMR (CDCl ₃ )
δ ppm: 7.54 (2H, d), 7.38-7.22 (4H, m), 7.06-7.00 (2H, m), 5.76 (1H, d), 3.08 -3.02 (2H, m), 2.75-2.68 (2H, m), 2.55-2.10 (4H, m), 1.90-1.86 (2H, m), 0 .87-0.65 (3H, m), 0.57-0.47 (1H, m)

式（２４−１）で示される化合物６．６０ｇおよびジイソプロピルエチルアミン５．４３ｇを無水Ｎ，Ｎ−ジメチルホルムアミド５０ｍｌに溶解させた。得られた混合物に氷冷下、ピバロイルクロライドを滴下し、室温で３０分間攪拌した。反応混合物に水を加え、ｔｅｒｔ−ブチルメチルエーテルで抽出した。有機層を無水硫酸マグネシウムで乾燥後、減圧濃縮し、粗生成物を得た。この粗生成物をシリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝３：１７）に付し、式（２３−２）で示される化合物７．１４ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３８−７．２６（５Ｈ，ｍ），６．８７（２Ｈ，ｓ），４．５３（２Ｈ， ｄｄ）、３．６３−３．５４（２Ｈ，ｍ），２．７５−２．２２（１２Ｈ，ｍ），１．８６−１．７６（２Ｈ，ｍ），１．１０−１．０３（６Ｈ，ｍ），０．８７（９Ｈ，ｓ） Production Example 1-44: Production of compound represented by formula (1-71) <Production of compound represented by formula 23-2>

6.60 g of the compound represented by the formula (24-1) and 5.43 g of diisopropylethylamine were dissolved in 50 ml of anhydrous N, N-dimethylformamide. Pivaloyl chloride was added dropwise to the obtained mixture under ice cooling, and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture, and the mixture was extracted with tert-butyl methyl ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a crude product. This crude product was subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 3: 17) to obtain 7.14 g of a compound represented by the formula (23-2).
1H NMR (CDCl ₃ )
δ ppm: 7.38-7.26 (5H, m), 6.87 (2H, s), 4.53 (2H, dd), 3.63-3.54 (2H, m), 2.75 -2.22 (12H, m), 1.86-1.76 (2H, m), 1.10-1.03 (6H, m), 0.87 (9H, s)

式（２３−２）で示される化合物７．１４ｇを酢酸エチル４５ｍｌに溶解した。得られた混合液に１０％パラジウム炭素３．５７ｇを加え、水素雰囲気下、３５℃で１８時間攪拌した。反応混合液をセライト（登録商標）ろ過し、得られたろ液を減圧濃縮し、式（２２−２）で示される化合物５．１０ｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：６．８７（２Ｈ，ｓ），３．８１（２Ｈ，ｄ），２．７８−２．２４（１２Ｈ，ｍ），１．８３−１．７３（２Ｈ、ｍ）、１．３９−１．３６（１Ｈ，ｍ）、１．１０−１．０４（６Ｈ，ｍ）、０．８７（９Ｈ，ｓ） <Production of Compound represented by Formula 22-2>

7.14 g of the compound represented by the formula (23-2) was dissolved in 45 ml of ethyl acetate. To the obtained mixed solution, 3.57 g of 10% palladium carbon was added and stirred at 35 ° C. for 18 hours in a hydrogen atmosphere. The reaction mixture was filtered through Celite (registered trademark), and the obtained filtrate was concentrated under reduced pressure to obtain 5.10 g of a compound represented by the formula (22-2).
1H NMR (CDCl ₃ )
δ ppm: 6.87 (2H, s), 3.81 (2H, d), 2.78-2.24 (12H, m), 1.83-1.73 (2H, m), 1.39 -1.36 (1H, m), 1.10-1.04 (6H, m), 0.87 (9H, s)

式（２１−２）で示される化合物１９３ｍｇおよびジイソプロピルエチルアミン１６２ｍｇをＮ，Ｎ−ジメチルホルムアミド５ｍｌ溶液に溶解させた。得られた混合物に氷冷下、メタンスルホニルクロライド６８．７ｍｇを滴下し、室温下１時間攪拌した。反応混合物に水を加え、ｔｅｒｔ−ブチルメチルエーテルで抽出した。有機層を無水硫酸マグネシウムで乾燥後、減圧濃縮した。残渣にヘキサンを加え、濾過することにより、式（２１−１）で示される化合物２０８ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：６．８７（２Ｈ，ｓ），４．３７（２Ｈ，ｄｄ）、３．０５（３Ｈ，ｓ），２．７４−２．２５（１２Ｈ，ｍ），２．００−１．９７（２Ｈ，ｍ），１．１０−１．０４（６Ｈ，ｍ），０．８８（９Ｈ，ｓ）
<Production of Compound represented by Formula 21-1>

193 mg of the compound represented by the formula (21-2) and 162 mg of diisopropylethylamine were dissolved in 5 ml of N, N-dimethylformamide. Under ice cooling, 68.7 mg of methanesulfonyl chloride was added dropwise to the resulting mixture, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, and the mixture was extracted with tert-butyl methyl ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Hexane was added to the residue and filtered to obtain 208 mg of the compound represented by the formula (21-1).
1H NMR (CDCl ₃ )
δ ppm: 6.87 (2H, s), 4.37 (2H, dd), 3.05 (3H, s), 2.74-2.25 (12H, m), 2.00-1.97 (2H, m), 1.10-1.04 (6H, m), 0.88 (9H, s)

式（２１−１）で示される化合物２００ｍｇおよびジイソプロピルエチルアミン１６７ｍｇをＮ，Ｎ−ジメチルホルムアミド５ｍｌに溶解した。得られた混合液にパラブロモチオフェノール１９５ｍｇを加え、室温下、１６時間攪拌した。得られた混合物を８０℃に加熱し２時間攪拌した後、水を加えｔｅｒｔ−ブチルメチルエーテルで抽出した。得られた有機層を水で洗浄し、無水硫酸マグネシウムで乾燥し、濾過した。得られたろ液を減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝０：１００→１：４）に付し、式（１−７１）で示される化合物１９３ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．４２（２Ｈ，ｄｔ），７．２１（２Ｈ，ｄｔ），６．９８（２Ｈ，ｓ），５．６１（１Ｈ，ｓ），３．０５−２．９３（２Ｈ，ｍ），２．７３−２．６４（２Ｈ，ｍ）、２．４８−２．２１（１０Ｈ，ｍ），１．８１（２Ｈ，ｑ），１．１０−１．０３（６Ｈ，ｍ） <Production of Compound represented by Formula 1-71>

200 mg of the compound represented by the formula (21-1) and 167 mg of diisopropylethylamine were dissolved in 5 ml of N, N-dimethylformamide. To the obtained mixture, 195 mg of parabromothiophenol was added and stirred at room temperature for 16 hours. The resulting mixture was heated to 80 ° C. and stirred for 2 hours, water was added, and the mixture was extracted with tert-butyl methyl ether. The obtained organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure and subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 0: 100 → 1: 4) to obtain 193 mg of the compound represented by the formula (1-71).
1H NMR (CDCl ₃ )
δ ppm: 7.42 (2H, dt), 7.21 (2H, dt), 6.98 (2H, s), 5.61 (1H, s), 3.05-2.93 (2H, m ), 2.73-2.64 (2H, m), 2.48-2.21 (10H, m), 1.81 (2H, q), 1.10-1.03 (6H, m)

式（２２−２）で示される化合物１９３ｍｇおよびジイソプロピルエチルアミン２５８ｍｇをＮ，Ｎ−ジメチルホルムアミド５ｍｌ溶液に溶解した。得られた混合物に氷冷下、メタンスルホニルクロライド６８．７ｍｇを滴下し、室温下３０分間攪拌した。得られた混合液に２−メルカプトピリミジン１２３ｍｇを加え、８０℃で９時間攪拌した。得られた反応液に２Ｎ塩酸を加え、ｐＨ１に調整した後、ｔｅｒｔ−ブチルメチルエーテルで抽出した。得られた有機層を水で洗浄し、無水硫酸マグネシウムで乾燥し、濾過した。得られたろ液を減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝７：１３）に付し、式（１−１３２）で示される化合物１７１ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．５２（２Ｈ，ｄｄ），６．９８（１Ｈ，ｄｔ），６．８７（２Ｈ，ｄ），３．３０−３．１８（２Ｈ，ｍ），２．８５−２．６７（２Ｈ，ｍ），２．５７−２．２３（１０Ｈ，ｍ），１．９６（２Ｈ，ｑ），１．０９−１．０２（６Ｈ，ｍ），０．８７（９Ｈ，ｓ）
製造例１−４６：式（１−３４）で示される化合物の製造 Production Example 1-45: Production of compound represented by formula (1-132) <Production of compound represented by formula 1-132>

193 mg of the compound represented by the formula (22-2) and 258 mg of diisopropylethylamine were dissolved in 5 ml of N, N-dimethylformamide. Under ice cooling, 68.7 mg of methanesulfonyl chloride was added dropwise to the resulting mixture, and the mixture was stirred at room temperature for 30 minutes. To the resulting mixture, 123 mg of 2-mercaptopyrimidine was added and stirred at 80 ° C. for 9 hours. 2N Hydrochloric acid was added to the obtained reaction solution to adjust to pH 1, followed by extraction with tert-butyl methyl ether. The obtained organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure and subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 7: 13) to obtain 171 mg of a compound represented by the formula (1-132).
1H NMR (CDCl ₃ )
δ ppm: 8.52 (2H, dd), 6.98 (1H, dt), 6.87 (2H, d), 3.30-3.18 (2H, m), 2.85-2.67 (2H, m), 2.57-2.23 (10H, m), 1.96 (2H, q), 1.09-1.02 (6H, m), 0.87 (9H, s)
Production Example 1-46: Production of the compound represented by the formula (1-34)

式（１−１３２）で示される化合物１７０ｍｇをテトラヒドロフラン１０ｍｌ、メタノール１０ｍｌ、水１０ｍｌの混合溶液に溶解させた。得られた溶液に水酸化リチウム一水和物４４．５ｍｇを添加し、室温にて１０分間攪拌した。反応液を減圧濃縮し、２Ｎ塩酸を加えｐＨ１とした後、ｔｅｒｔ−ブチルメチルエーテルで抽出した。得られた有機層を水で洗浄し、無水硫酸マグネシウムで乾燥し、濾過した。得られたろ液を減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝２：３）に付し、式（１−３４）で示される化合物１２６ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．５３（２Ｈ，ｄ），７．００−６．９６（３Ｈ，ｍ），５．５７（１Ｈ，ｓ），３．２９−３．２１（２Ｈ，ｍ），２．８１−２．７３（２Ｈ，ｍ），２．５１−２．４３（２Ｈ，ｍ），２．４１−２．２５（８Ｈ，ｍ），１．９５（２Ｈ，ｓ），１．０９−１．０３（６Ｈ，ｍ） <Production of Compound represented by Formula 1-34>

170 mg of the compound represented by the formula (1-132) was dissolved in a mixed solution of 10 ml of tetrahydrofuran, 10 ml of methanol and 10 ml of water. To the obtained solution, 44.5 mg of lithium hydroxide monohydrate was added and stirred at room temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure, adjusted to pH 1 with 2N hydrochloric acid, and extracted with tert-butyl methyl ether. The obtained organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure and subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 2: 3) to obtain 126 mg of a compound represented by the formula (1-34).
1H NMR (CDCl ₃ )
δ ppm: 8.53 (2H, d), 7.00-6.96 (3H, m), 5.57 (1H, s), 3.29-3.21 (2H, m), 2.81 -2.73 (2H, m), 2.51-2.43 (2H, m), 2.41-2.25 (8H, m), 1.95 (2H, s), 1.09-1 .03 (6H, m)

式（２２−２）で示される化合物１７８ｍｇおよびジイソプロピルエチルアミン２３８ｍｇをＮ，Ｎ−ジメチルホルムアミド５ｍｌ溶液に溶解させた。得られた混合物に氷冷下、メタンスルホニルクロライド６３．３ｍｇを滴下し、室温下３０分間攪拌した。得られた溶液にパラ（メチルチオ）チオフェノール１５８ｍｇを加え、室温下、１．５時間攪拌した。得られた反応液に２Ｎ塩酸を加えｐＨ１とし、ｔｅｒｔ−ブチルメチルエーテルで抽出した。得られた有機層を水で洗浄し、無水硫酸マグネシウムで乾燥し、濾過した。ろ液を減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：９→７：１３）に付し、式（１−１０４）で示される化合物１００ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．３０（２Ｈ，ｄｔ），７．２０（２Ｈ，ｄｔ），６．９８（２Ｈ，ｓ），５．５８（１Ｈ，ｓ），２．９７（２Ｈ，ｔｄ），２．７０−２．６４（２Ｈ，ｍ），２．４７（３Ｈ，ｓ），２．４５−２．２２（１０Ｈ，ｍ），１．８０（２Ｈ，ｑ），１．１０−１．０３（６Ｈ，ｍ） Production Example 1-47: Production of compound represented by formula (1-104) <Production of compound represented by formula 1-104>

178 mg of the compound represented by the formula (22-2) and 238 mg of diisopropylethylamine were dissolved in 5 ml of N, N-dimethylformamide. Under ice cooling, 63.3 mg of methanesulfonyl chloride was added dropwise to the resulting mixture, and the mixture was stirred at room temperature for 30 minutes. To the resulting solution, 158 mg of para (methylthio) thiophenol was added and stirred at room temperature for 1.5 hours. The resulting reaction solution was adjusted to pH 1 with 2N hydrochloric acid and extracted with tert-butyl methyl ether. The obtained organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 9 → 7: 13) to obtain 100 mg of the compound represented by the formula (1-104).
1H NMR (CDCl ₃ )
δ ppm: 7.30 (2H, dt), 7.20 (2H, dt), 6.98 (2H, s), 5.58 (1H, s), 2.97 (2H, td), 2. 70-2.64 (2H, m), 2.47 (3H, s), 2.45-2.22 (10H, m), 1.80 (2H, q), 1.10-1.03 ( 6H, m)

式（２２−２）で示される化合物３８７ｍｇおよびジイソプロピルエチルアミン５１６ｍｇをＮ，Ｎ−ジメチルホルムアミド１０ｍｌ溶液に溶解させた。得られた混合物に氷冷下、メタンスルホニルクロライド１３７ｍｇを滴下し、室温下１時間攪拌した。得られた混合液に４−トリフルオロメチル−２−ピリミジンチオール３９６ｍｇを加え、８０℃で３０分間攪拌した。反応液に２Ｎ塩酸を加え、ｐＨ１になるように調整した後、ｔｅｒｔ−ブチルメチルエーテルで抽出した。得られた有機層を水で洗い、無水硫酸マグネシウムで乾燥し、濾過した。得られたろ液を減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１−１３３）で示される化合物５４６ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．７６（１Ｈ，ｄ），７．２９（１Ｈ，ｄ），６．８７（２Ｈ，ｄ），３．３３−３．２３（２Ｈ，ｍ），２．８２−２．６８（３Ｈ，ｍ），２．５９−２．２４（９Ｈ，ｍ），１．９７（２Ｈ，ｑ），１．１０−１．０３（６Ｈ，ｍ），０．８８（９Ｈ，ｓ） Production Example 1-48: Production of compound represented by formula (1-133) <Production of compound represented by formula 1-133>

387 mg of the compound represented by the formula (22-2) and 516 mg of diisopropylethylamine were dissolved in 10 ml of N, N-dimethylformamide. To the obtained mixture, 137 mg of methanesulfonyl chloride was added dropwise under ice cooling, and the mixture was stirred at room temperature for 1 hour. To the obtained mixed solution, 396 mg of 4-trifluoromethyl-2-pyrimidinethiol was added and stirred at 80 ° C. for 30 minutes. 2N Hydrochloric acid was added to the reaction mixture to adjust to pH 1, followed by extraction with tert-butyl methyl ether. The obtained organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure and subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 546 mg of a compound represented by the formula (1-133).
1H NMR (CDCl ₃ )
δ ppm: 8.76 (1H, d), 7.29 (1H, d), 6.87 (2H, d), 3.33-3.23 (2H, m), 2.82-2.68 (3H, m), 2.59-2.24 (9H, m), 1.97 (2H, q), 1.10-1.03 (6H, m), 0.88 (9H, s)

式（１−１３３）で示される化合物５４６ｍｇをテトラヒドロフラン１０ｍｌ、メタノール１０ｍｌと水１０ｍｌとの混合溶液に溶解した。得られた溶液に水酸化リチウム一水和物１２６ｍｇを添加し、室温にて２０分間攪拌した。反応液を減圧濃縮し、２Ｎ塩酸を加えｐＨ１とした後、ｔｅｒｔ−ブチルメチルエーテルで抽出した。得られた有機層を水で洗い洗浄し、無水硫酸マグネシウムで乾燥し、濾過した。得られたろ液を減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝１：３）に付し、式（１−３５）で示される化合物４３５ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：８．７６（１Ｈ，ｄ），７．２９（１Ｈ，ｄ），６．９９（２Ｈ，ｄ），５．６２（１Ｈ，ｓ），３．２７（２Ｈ，ｔｄ），２．７８−２．７１（２Ｈ，ｍ），２．５１−１．９３（１２Ｈ，ｍ），１．０７（６Ｈ，ｍ）
Production Example 1-49: Production of compound represented by formula (1-35) <Production of compound represented by formula 1-35>

546 mg of the compound represented by the formula (1-133) was dissolved in a mixed solution of 10 ml of tetrahydrofuran, 10 ml of methanol and 10 ml of water. 126 mg of lithium hydroxide monohydrate was added to the resulting solution, and the mixture was stirred at room temperature for 20 minutes. The reaction mixture was concentrated under reduced pressure, adjusted to pH 1 with 2N hydrochloric acid, and extracted with tert-butyl methyl ether. The obtained organic layer was washed with water, washed, dried over anhydrous magnesium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure and subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 1: 3) to obtain 435 mg of a compound represented by the formula (1-35).
1H NMR (CDCl ₃ )
δ ppm: 8.76 (1H, d), 7.29 (1H, d), 6.99 (2H, d), 5.62 (1H, s), 3.27 (2H, td), 2. 78-2.71 (2H, m), 2.51-1.93 (12H, m), 1.07 (6H, m)

The compound of the present invention produced according to Production Example 1-49 is shown below.
<Production of Compound represented by Formula 1-136>
1H NMR (CDCl ₃ )
δ ppm: 7.38 (1H, t), 7.26 (1H, m), 7.10 (2H, m), 6.98 (2H, s), 5.51 (1H, s), 3. 00 (2H, t), 2.77 (2H, t), 2.50-2.20 (10H, m), 1.79 (2H, q), 1.06 (6H, q)
<Production of Compound represented by Formula 1-137>
1H NMR (CDCl ₃ )
δ ppm: 7.37 (1H, d), 7.30-7.20 (2H, m), 7.15-7.06 (1H, m), 6.98 (2H, s), 5.51 (1H, s), 3.02 (2H, q), 2.71 (2H, t), 2.51-2.22 (10H, m), 1.87 (2H, q), 1.06 ( 6H, q)
<Production of Compound represented by Formula 1-138>
1H NMR (CDCl ₃ )
δ ppm: 7.57 (1H, d), 7.55-7.25 (2H, m), 7.07-7.04 (1H, m), 6.98 (2H, s), 5.51 (1H, s), 3.04-3.00 (2H, m), 2.71 (2H, t), 2.50-2.28 (10H, m), 1.89 (2H, q), 1.06 (6H, q)
<Production of Compound represented by Formula 1-139>
1H NMR (CDCl ₃ )
δ ppm: 7.28-7.26 (1H, d), 7.19-7.05 (3H, m), 6.97 (2H, s), 5.51 (1H, s), 2.98 (2H, t), 2.70 (2H, t), 2.50-2.20 (13H, m), 1.85 (2H, q), 1.06 (6H, q)
<Production of Compound represented by Formula 1-140>
1H NMR (CDCl ₃ )
δ ppm: 7.30-7.18 (4H, m), 6.97 (2H, s), 5.46 (1H, s), 3.00 (2H, t), 2.78 (2H, q ), 2.65 (2H, t), 2.50-2. 21 (10H, m), 1.84 (2H, q), 1.23 (3H, t), 1.06 (6H, q)
<Production of Compound represented by Formula 1-141>
1H NMR (CDCl ₃ )
δ ppm: 7.34-7.10 (4H, m), 6.97 (2H, s), 5.53 (1H, s), 3.55-3.45 (1H, m), 2.98 (2H, t), 2.70 (2H, t), 2.50-2.22 (10H, m), 1.85 (2H, q), 1.24 (6H, d), 1.06 ( 6H, q)
<Production of Compound represented by Formula 1-142>
1H NMR (CDCl ₃ )
δ ppm: 7.32-7.19 (2H, m), 6.98-6.84 (4H, m), 5.53 (1H, s), 3.91 (3H, s), 3.08 -2.94 (2H, m), 2.69 (2H, t), 2.48-2.20 (10H, m), 1.80 (2H, q), 1.06 (6H, q)
<Production of Compound represented by Formula 1-143>
1H NMR (CDCl ₃ )
δ ppm: 7.30-7.20 (1H, m), 7.10-6.98 (4H, m), 6.90-6.80 (1H, t), 5.52 (1H, s) , 3.05-3.00 (2H, m), 2.70 (2H, t), 2.49-2.23 (10H, m), 1.83 (2H, q), 1.06 (6H) , Q)
<Production of Compound represented by Formula 1-144>
1H NMR (CDCl ₃ )
δ ppm: 7.30-7.15 (4H, m), 6.97 (2H, s), 5.54 (1H, s), 3.05-3.00 (2H, m), 2.70 (2H, t), 2.48-2.22 (10H, m), 1.85 (2H, q), 1.06 (6H, q)
<Production of Compound represented by Formula 1-145>
1H NMR (CDCl ₃ )
δ ppm: 7.48 (1H, s), 7.31-7.11 (3H, m), 6.95 (2H, s), 5.53 (1H, s), 3.09-3.00 (2H, m), 2.70 (2H, t), 2.47-2.25 (10H, m), 1.85 (2H, q), 1.06 (6H, q)
<Production of Compound represented by Formula 1-146>
1H NMR (CDCl ₃ )
δ ppm: 7.20-7.10 (3H, m), 7.12-6.98 (3H, m), 5.51 (1H, s), 3.01-2.95 (2H, m) , 2.65 (2H, t), 2.45-2.20 (13H, m), 1.82 (2H, q), 1.06 (6H, q)
<Production of Compound represented by Formula 1-147>
1H NMR (CDCl ₃ )
δ ppm: 7.30-7.12 (3H, m), 6.98 (2H, s), 5.48 (1H, s), 3.10-3.00 (2H, m), 2.72 (2H, t), 2.52-2.22 (10H, m), 1.89 (2H, q), 1.06 (6H, q)
<Production of Compound represented by Formula 1-148>
1H NMR (CDCl ₃ )
δ ppm: 7.12-7.05 (3H, m), 6.92 (2H, s), 5.50 (1H, s), 2.71 (2H, t), 2.55 (6H, s) ), 2.61 (2H, t), 2.42-2.17 (10H, m), 1.80 (2H, q), 1.06 (6H, q)
<Production of Compound represented by Formula 1-149>
1H NMR (CDCl ₃ )
δ ppm: 7.36 (1H, dd), 7.14 (1H, dd), 6.99 (1H, dd), 6.96 (2H, s), 5.80 (1H, s), 2. 86 (2H, t), 2.67-2.59 (2H, m), 2.47-2.18 (10H, m), 1.78 (2H, q), 1.07 (3H, t) , 1.05 (3H, t)
<Production of compound represented by formula 1-150>
1H NMR (CDCl ₃ )
δ ppm: 7.68 (1H, d), 7.24 (1H, d), 6.99 (2H, s), 5.49 (1H, s), 3.32 (2H, t), 2. 76-2.68 (2H, m), 2.46-2.25 (10H, m), 1.97 (2H, q), 1.08 (3H, t), 1.05 (3H, t)
<Production of Compound represented by Formula 1-151>
1H NMR (CDCl ₃ )
δ ppm: 7.88 (2H, d), 7.33 (2H, d), 6.99 (2H, s), 5.52 (1H, s), 3.10 (2H, dt), 2. 75-2.69 (2H, m), 2.58 (3H, s), 2.47-2.24 (10H, m), 1.90 (2H, q), 1.09 (3H, t) , 1.05 (3H, t)
<Production of Compound represented by Formula 1-152>
1H NMR (CDCl ₃ )
δ ppm: 7.31 (2H, d), 6.97 (2H, s), 6.78 (2H, d), 5.57 (1H, s), 5.18 (1H, s), 2. 89 (2H, t), 2.68-1.61 (2H, m), 2.43-2.18 (10H, m), 1.76 (2H, q), 1.08 (3H, t) , 1.04 (3H, t)
<Production of Compound represented by Formula 1-153>
1H NMR (CDCl ₃ )
δ ppm: 8.67 (1H, dd), 7.67 (1H, dd), 7.27-7.25 (1H, m), 6.99 (2H, s), 5.50 (1H, s) ), 3.33-3.29 (2H, m), 2.79-2.71 (2H, m), 2.51-2.24 (10H, m), 1.94-1.89 (2H) , M), 1.07 (3H, t), 1.04 (3H, t)
<Production of Compound represented by Formula 1-155>
1H NMR (CDCl ₃ )
δ ppm: 9.02-9.01 (1H, m), 8.04 (1H, dd), 7.23 (1H, dd), 6.98 (2H, s), 5.53 (1H, s) ), 3.93 (3H, s), 3.32 (2H, t), 2.76 (2H, t), 2.51-2.23 (10H, m), 1.92 (2H, q) , 1.05 (6H, q)
<Production of Compound represented by Formula 1-127>
1H NMR (CDCl ₃ )
δ ppm: 8.36 (1H, dd), 7.55 (1H, dd), 6.98-6.95 (3H, m), 5.46 (1H, s), 3.30 (2H, dt) ), 2.80-2.73 (2H, m), 2.52-2.25 (10H, m), 1.92 (2H, q), 1.07 (3H, t), 1.04 ( 3H, t)
<Production of Compound represented by Formula 1-160>
1H NMR (CDCl ₃ )
δ ppm: 6.98 (2H, s), 5.75 (1H, s), 5.55 (1H, s), 3.94 (6H, s), 3.29-3.18 (2H, m ), 2.76-2.69 (2H, m), 2.47-2.26 (10H, m), 1.96 (2H, q), 1.07 (6H, q)
<Production of Compound represented by Formula 1-161>
1H NMR (CDCl ₃ )
δ ppm: 6.98 (2H, s), 6.84-6.78 (2H, m), 6.62 (1H, tt), 5.52 (1H, s), 3.03 (2H, ddd) ), 2.72 (2H, dt), 2.48-2.25 (10H, m), 1.87 (2H, dd), 1.07 (6H, dt)
<Production of Compound represented by Formula 1-70>
1H NMR (CDCl ₃ )
δ ppm: 7.61 (2H, d), 7.07 (2H, d), 6.97 (2H, s), 5.72 (1H, s), 3.04-2.92 (2H, m ), 2.72-2.63 (2H, m), 2.45-2.21 (10H, m), 1.81 (2H, q), 1.08 (3H, t), 1.04 ( 3H, t)
<Production of Compound represented by Formula 1-75>
1H NMR (CDCl ₃ )
δ ppm: 7.34-7.28 (4H, m), 6.98 (2H, s), 5.46 (1H, s), 2.99 (2H, dt), 2.71-2.64 (2H, m), 2.43-2.23 (10H, m), 1.82 (2H, q), 1.31 (9H, s), 1.08 (3H, t), 1.04 ( 3H, t)
<Production of Compound represented by Formula 1-109>
1H NMR (CDCl ₃ )
δ ppm: 8.74 (2H, d), 6.98 (2H, s), 5.50 (1H, s), 3.28 (2H, dt), 2.79-2.73 (2H, m ), 2.52-2.25 (10H, m), 1.96 (2H, q), 1.09-1.03 (6H, m)
<Production of Compound represented by Formula 1-112>
1H NMR (CDCl ₃ )
δ ppm: 8.62 (1H, d), 7.74 (1H, dd), 7.60 (1H, d), 6.98 (2H, s), 5.51 (1H, s), 3. 15-3.07 (2H, m), 2.75-2.68 (2H, m), 2.47-2.24 (10H, m), 1.89 (2H, q), 1.09 ( 3H, t), 1.05 (3H, t)
<Production of Compound represented by Formula 1-115>
1H NMR (CDCl ₃ )
δ ppm: 8.70 (1H, s), 8.51 (1H, s), 6.98 (2H, s), 5.49 (1H, s), 3.33 (2H, dt), 2. 79-2.72 (2H, m), 2.51-2.24 (10H, m), 1.93 (2H, q), 1.07 (3H, t), 1.04 (3H, t)
<Production of Compound represented by Formula 1-118>
1H NMR (CDCl ₃ )
δ ppm: 7.56 (1H, d), 7.49 (1H, d), 6.98 (2H, s), 5.48 (1H, s), 3.54-3.46 (2H, m ), 2.79-2.70 (2H, m), 2.53-2.27 (10H, m), 2.06-1.99 (2H, m), 1.08 (3H, t), 1.06 (3H, t)
<Production of compound represented by formula 1-121>
1H NMR (CDCl ₃ )
δ ppm: 8.61 (1H, d), 7.72 (1H, dd), 7.23 (1H, dd), 6.98 (2H, s), 3.29 (2H, ddd), 2. 76 (2H, ddd), 2.52-2.23 (10H, m), 1.95-1.89 (2H, m), 1.06 (6H, dt)
<Production of Compound represented by Formula 1-169>
1H NMR (CDCl ₃ )
δ ppm: 7.21-7.06 (3H, m), 6.95 (2H, s), 5.64 (1H, s), 2.97 (2H, ddd), 2.68 (2H, dt) ), 2.48-2.22 (10H, m), 1.83-1.74 (2H, m), 1.12-0.99 (6H, m)
<Production of Compound represented by Formula 1-172>
1H NMR (CDCl ₃ )
δ ppm: 6.95 (2H, s), 5.79 (1H, s), 4.07 (2H, t), 2.68 (2H, d), 2.37-2.16 (16H, m ), 1.95 (2H, d), 1.09-0.98 (6H, m)
<Production of Compound represented by Formula 1-173>
1H NMR (CDCl ₃ )
δ ppm: 7.67 (2H, d), 7.32 (2H, d), 6.97 (2H, s), 6.30 (1H, s), 4.19-4.14 (2H, m ), 2.79-2.66 (2H, m), 2.48-2.28 (13H, m), 2.08-1.98 (2H, m), 1.03 (6H, td)

室温下、式（２１−１）で示される化合物３６０ｍｇをＮ，Ｎ−ジメチルホルムアミド４ｍｌに溶解し、アジ化ナトリウム５００ｍｇと１５クラウン５エーテル０．０１５ｍｌを加えた。得られた混合液を１００℃まで加熱して約４時間攪拌した。その後、得られた反応混合液を減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝３４：６６）に付し、式（３５−１）で示される化合物１８０ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：６．９８（２Ｈ，ｓ），５．７９（１Ｈ，ｓ），３．４４−３．４０（２Ｈ，ｍ），２．７１−２．６４（２Ｈ，ｍ），２．４４−２．２４（１０Ｈ，ｍ），１．７７（２Ｈ，ｑ）、１．０７（６Ｈ，ｔｄ）

＜式１―１３４で示される化合物の製造＞

室温下、式（３５−１）で示される化合物１００ｍｇと１−エチニルー４−フルオロベンゼン４０ｍｇをアセトニトリル４ｍｌとジメチルスルホキシド１ｍｌに溶解し、得られた混合液にアスコルビン酸ナトリウムを７ｍｇと硫酸銅３ｍｇを加え、約５時間加熱還流を行った。その後、得られた反応混合液を減圧濃縮し、シリカゲルカラムクロマトグラフィ（溶出液、酢酸エチル：ヘキサン＝６６：３４）に付し、式（１−１３４）で示される化合物５４．１ｍｇを得た。
１Ｈ ＮＭＲ（ＣＤＣｌ₃）
δ ｐｐｍ：７．８３−７．７８（２Ｈ，ｍ），７．７５（１Ｈ，ｓ），７．１３（２Ｈ，ｔ），６．９８（２Ｈ， s）、５．７７（１Ｈ，ｓ）、４．５７−４．４６（２Ｈ，ｍ），２．８０−２．６７（２Ｈ，ｍ），２．５２−２．１２（１２Ｈ，ｍ）、１．０４（６Ｈ，ｑ）
Production Example 1-50: Production of compound represented by formula (1-134) <Production of compound represented by formula 35-1>

At room temperature, 360 mg of the compound represented by the formula (21-1) was dissolved in 4 ml of N, N-dimethylformamide, and 500 mg of sodium azide and 0.015 ml of 15 crown 5 ether were added. The resulting mixture was heated to 100 ° C. and stirred for about 4 hours. Then, the obtained reaction mixture was concentrated under reduced pressure and subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 34: 66) to obtain 180 mg of the compound represented by the formula (35-1).
1H NMR (CDCl ₃ )
δ ppm: 6.98 (2H, s), 5.79 (1H, s), 3.44-3.40 (2H, m), 2.71-2.64 (2H, m), 2.44 -2.24 (10H, m), 1.77 (2H, q), 1.07 (6H, td)

<Production of compound represented by Formula 1-134>

At room temperature, 100 mg of the compound represented by the formula (35-1) and 40 mg of 1-ethynyl-4-fluorobenzene are dissolved in 4 ml of acetonitrile and 1 ml of dimethyl sulfoxide, and 7 mg of sodium ascorbate and 3 mg of copper sulfate are added to the resulting mixture. In addition, the mixture was heated to reflux for about 5 hours. Thereafter, the obtained reaction mixture was concentrated under reduced pressure and subjected to silica gel column chromatography (eluent, ethyl acetate: hexane = 66: 34) to obtain 54.1 mg of a compound represented by the formula (1-134).
1H NMR (CDCl ₃ )
δ ppm: 7.83-7.78 (2H, m), 7.75 (1H, s), 7.13 (2H, t), 6.98 (2H, s), 5.77 (1H, s) ), 4.57-4.46 (2H, m), 2.80-2.67 (2H, m), 2.52-2.12 (12H, m), 1.04 (6H, q)

This invention compound manufactured according to manufacture example 1-50 is shown below.
Production of Compound of Formula (1-135) 1H NMR (CDCl ₃ )
δ ppm: 7.95 (2H, d), 7.88 (1H, s), 7.69 (2H, d), 6.97 (2H, s), 5.79 (1H, s), 4. 60-4.48 (2H, m), 2.80-2.68 (2H, m), 2.53-2.12 (12H, m), 1.04 (6H, q)

  Next, formulation examples are shown. In addition, this invention compound is shown by the number of structural formula.

Formulation Example 1
Wetting agent Compound (1-1) 50% by weight
Sodium lignin sulfonate 5% by weight
Polyoxyethylene alkyl ether 5% by weight
5% white carbon
Clay 35% by weight
To obtain a wettable powder.
Each compound is obtained by replacing compound (1-1) with compound (1-2) to compound (1-156) or compound (1-158) to compound (1-173).

Formulation Example 2
Granule Compound (1-1) 1.5% by weight
2% by weight sodium lignin sulfonate
Talc 40% by weight
Bentonite 56.5% by weight
, Mixed with water, granulated and dried to obtain granules.
Each compound is obtained by replacing compound (1-1) with compound (1-2) to compound (1-156) or compound (1-158) to compound (1-173).

Formulation Example 3
Flowable agent Compound (1-1) 10% by weight
35% by weight of white carbon containing 50% by weight of polyoxyethylene alkyl ether sulfate ammonium salt
55% by weight of water
Are mixed and finely pulverized by a wet pulverization method to obtain a flowable agent.
Each compound is obtained by replacing compound (1-1) with compound (1-2) to compound (1-156) or compound (1-158) to compound (1-173).

Next, test examples are shown.
The weed control efficacy of the compounds of the present invention was visually observed and evaluated in 11 stages from 0 to 10 (0 was no action, 10 was completely dead, and 1 to 9 was evaluated between them).

Test Example 1-1 Field-emergence post-treatment test After filling a commercially available seedling culture soil into a plastic cup having a diameter of 8 cm and a depth of 6.5 cm, seeded with Inobiae and covering with about 0.5 cm of soil, Cultivated within. When the plant grew to the 1st to 2nd leaf stage, a drug diluent containing the compound (1-1) was sprayed uniformly over the entire plant at a predetermined treatment dose. The drug diluent is prepared by dissolving a predetermined amount of the compound (1-1) in a dimethylformamide solution (2%) of Tween 20 (polyoxyethylene sorbitan fatty acid ester, manufactured by MP Biomedicals, Inc.) with deionized water. Prepared by dilution. The plant after spraying was cultivated in a greenhouse, and after 20 days of treatment, the efficacy of control of Inobiae was observed, and the control effect was evaluated.
Similarly, the present compounds (1-2) to (1-23), (1-29) to (1-31), (1-33) to (1-36), (1-40) to (1 -41), (1-44), (1-58) to (1-71), (1-73) to (1-75), (1-78), (1-83) to (1-84) ), (1-91) to (1-92), (1-94) to (1-95), (1-97) to (1-100), (1-102) to (1-105), (1-107) to (1-109), (1-112), (1-115), (1-118), (1-121), (1-127) to (1-128) (1- 134) to (1-156), (1-158) to (1-162), (1-165) to (1-169), (1-171), (1-13-A), (1- 13-B) was also tested.
As a result, the compounds (1-1) to (1-23), (1-29) to (1-31), (1-33) to (1-36), (1-40) to (1-41) ), (1-44), (1-58) to (1-71), (1-73) to (1-75), (1-78), (1-83) to (1-84), (1-91) to (1-92), (1-94) to (1-95), (1-97) to (1-100), (1-102) to (1-105), (1 -107) to (1-109), (1-112), (1-115), (1-118), (1-121), (1-127) to (1-128) (1-134) To (1-156), (1-158) to (1-162), (1-165) to (1-169), (1-171), (1-13-A), (1-13- B) showed a potency of 9 or more at a treatment dose of 1,000 g / 10000 m ² .

Test example 1-2 Field budding post-treatment test A plastic cup having a diameter of 8 cm and a depth of 6.5 cm was filled with a commercial seedling culture soil, seeded with Yamgra seeds, covered with about 0.5 cm of soil, and then placed in a greenhouse. Cultivated within. When the plant grew to the 1st to 2nd leaf stage, a drug diluent containing the compound (1-2) was sprayed uniformly over the entire plant at a predetermined treatment dose. The drug diluent was prepared by the same method as in Test Example 1-1. The plant after spraying was cultivated in a greenhouse, and after 20 days of treatment, the effect of controlling Yamgra was observed and evaluated.
Similarly, the present compounds (1-5), (1-12), (1-14), (1-98), (1-99), (1-100), (1-162) were also tested. did.
As a result, the compounds (1-2), (1-5), (1-12), (1-14), (1-98), (1-99), (1-100), (1-162) ) Showed a potency of 7 or more at a treatment dose of 1,000 g / 10000 m ² .

Test Example 2-1 Field budding pre-treatment test A plastic cup having a diameter of 8 cm and a depth of 6.5 cm was filled with steam-sterilized field soil, and seeds of Inobiae were sowed to cover about 0.5 cm of soil. Subsequently, the chemical | medical agent dilution liquid containing a compound (1-1) was uniformly spread | dispersed on the soil surface by the predetermined processing chemical amount. The drug diluent was prepared by the same method as in Test Example 1-1. The plant after chemical treatment was cultivated in a greenhouse, and the effect of controlling the white squirrel was observed and evaluated 3 weeks after spraying.
Similarly, the compounds (1-2) to (1-20), (1-23), (1-29) to (1-31), (1-33) to (1-36), (1 -40) to (1-41), (1-44), (1-58) to (1-71), (1-73) to (1-75), (1-78), (1-83) ) To (1-84), (1-91) to (1-92), (1-94) to (1-95), (1-97) to (1-98), (1-100), (1-102) to (1-104), (1-109), (1-112), (1-115), (1-118), (1-121), (1-127) to (1 -128), (1-134) to (1-146), (1-148) to (1-156), (1-158) to (1-162), (1-165) to (1-169) ), (1-13-A) and (1-13-B) were also tested.
As a result, the compounds (1-1) to (1-20), (1-23), (1-29) to (1-31), (1-33) to (1-36), (1-40 ) To (1-41), (1-44), (1-58) to (1-71), (1-73) to (1-75), (1-78), (1-83) to (1-84), (1-91) to (1-92), (1-94) to (1-95), (1-97) to (1-98), (1-100), (1 -102) to (1-104), (1-109), (1-112), (1-115), (1-118), (1-121), (1-127) to (1-128) ) (1-134) to (1-146), (1-148) to (1-156), (1-158) to (1-162), (1-165) to (1-169), ( 1-13-A) and (1-13-B) are 1,000. Both showed efficacy 7 or more application dose of / 10000 m ^2.

  The compound of the present invention has a weed control effect.

Claims (5)

Formula (I)

[Where:
m represents an integer of 1, 2 or 3,
n represents an integer of 1 to 3 ,
X represents S 2 , S (O) or S (O) ₂ ,
R ¹ represents hydrogen,
R ² and R ³ each independently represent hydrogen or a C _1-6 alkyl group, or R ² and R ³ are bonded to each other to represent a C _2-5 alkylene chain ;
R ⁴ is phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3-pyridazinyl group, 3-furyl group, 2-thienyl group, 2-thiazolyl group. 1,2,3-triazolyl group or 1-pyrazolyl group (provided that the phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 3- pyridazinyl group, 3-furyl group, 2-thienyl and 2-thiazolyl group is a halogen, a cyano group, a nitro group, an amino group, Baie Nzoiruamino group, Bae pointer fluoro thio group, C _1-6 alkyl, C _1-6 alkoxy groups, C _1-6 alkylthio group, a phenyl group, C _1-6 alkylsulfinyl group, C _1-6 alkylsulfonyl group, a hydroxyl group, (C _1-6 alkyl) carbonyl group, and (C _1-6 A 1) One or more substituents selected from the group consisting of (oxy) carbonyl groups may be present, and when having two or more substituents, the substituents may be the same or different. In addition, the C _1-6 alkyl group , C _1-6 alkoxy group, C _1-6 alkylthio group and phenyl group may have one or more halogens or C _1-3 haloalkyl groups, and two or more halogens. Or when having a C _1-3 haloalkyl group, the halogen or the C _1-3 haloalkyl group may be the same or different).
G is hydrogen or the following formula

{Wherein L represents oxygen,
R ⁵ is C _1-6 alkyl, C _1-6 alkoxy, C _3-6 alkenyloxy group, or a phenoxy group and table,
R ⁶ is table a C _1-6 alkyl group,
R ⁷ represents hydrogen,
W is to display the C _1-6 alkoxy group. }
Any one of the groups represented by
Z is halogen, nitro group, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 alkoxy group, 2-pyridyloxy group, C _3-8 cycloalkyl group, or Represents a phenyl group (provided that the C _1-6 alkyl group may have one or more halogens, and when it has two or more halogens, the halogens may be the same or different); may. the 2-pyridyloxy group may have one or more substituents selected from the group consisting of halogen及 beauty C _1-6 haloalkyl group, and when two or more substituents , the substituents may be the same or different. is et al, when n is an integer of 2 or more, Z may be the same or different.). ]
A cyclohexanone compound represented by: m is 2,
R ² and R ³ are independently of each other hydrogen, a methyl group, an ethyl group, or R ² and R ³ are combined to form an ethylene chain (provided that two R ² may be the same or different. And the two R ³ groups may be the same or different.)
R ⁴ is a phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, or 3-pyridazinyl group (provided that the phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 2-pyrazinyl group, and 3-pyridazinyl group are chlorine, bromine, iodine, fluorine, methyl group, ethyl group, isopropyl group, t-butyl group, methoxy group , Nitro group, amino group, cyano group, hydroxyl group, acetyl group, methoxycarbonyl group, pentafluorothio group, pentafluoroethyl group, difluoroethyl group, heptafluoroisopropyl group, trifluoromethylthio group, benzoylamino group, trifluoro Having one or more substituents selected from the group consisting of a methoxy group and a trifluoromethyl group The 1,2,3-triazolyl group and 1-pyrazolyl group may have a phenyl group which may have one or more substituents selected from the group consisting of a halogen atom and a trifluoromethyl group. You may have)
G is hydrogen, acetyl group, propionyl group, butylcarbonyl group, benzoyl group, methylsulfonyl group, methoxycarbonyl group, ethoxycarbonyl group, allyloxycarbonyl group, phenoxycarbonyl group, methoxymethyl group or ethoxymethyl group, 1. The cyclohexanone compound according to 1. The cyclohexanone compound according to claim 1 or 2 , wherein G is hydrogen. A herbicide containing the cyclohexanone compound according to any one of claims 1 to 3 as an active ingredient. A method for controlling weeds, wherein an effective amount of the cyclohexanone compound according to any one of claims 1 to 3 is applied to weeds or soil where weeds grow.